Michael b smith compendium of organic synthetic methods volume 9 wiley interscience (2000)

xvi INTRODUCTION Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from methylenes Ketones from ketones Alkyls from alkenes Hydrogenation of Alkenes Alkynes f

Compendium of Organic

Synthetic Methods

Compendium of Organic Synthetic Methods, Volume 9 Michael B Smith

Copyright2001 by John Wiley & Sons, Inc.ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

Compendium of Organic Synthetic Methods

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CONTENTS

PREFACE

ABBREVIATIONS

Compendium of Organic Synthetic Methods, Volume 9 Michael B Smith

Copyright2001 by John Wiley & Sons, Inc.ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

PREFACE

Since the original volume in this series by Ian and Shuyen Harrison, the goal

Voume 3 of the series Wade became the author for Volume 4 and continued with Volume 5 I began editing the series with Volume 6, where I introduced

sentative review of the literature and is offered in that context

require no special insructions for the use of Volume 9 Author citations and the Author Index have been continued as in Volumes 6-8

there are errors I take full responsibility If there are questions or comments,

Steven who have shown unfailing patience and devotion during this work I

benzoyl

0 BOC t-Butoxycarbonyl

Catalytic Cbz

0

& CH3

& Ot-Bu -CH2CH2CH2CH3 (NH)2Ce(NO3)6

0

+o

BrCH2CH2Br

c-C6H13-N=C=N-c-C6H13

Dimethylacetamide Dimethoxyethane MeOCH2CH20Me

0 N,N’-Dimethylformamide

H K N(CH3)2 bis-[ 1,3-Di@-methoxyphenyl)- 1,3-propanedionato]

dipivaloylmethanato 1,4-bis-(Diphenylphosphino)butane Ph2P(CH2)4PPh2 1,2-bis-(Diphenylphosphino)ethane Ph2PCH2CH2PPh2 bis-(Diphenylphosphino)ferrocene

1,3-bis-(Diphenylphosphino)propane Ph2P(CH2)3PPh2 Divinylbenzene

Flavin mononucleotide tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-octanedionate Cyclopentadienyl-bis-carbonyl iron

Flash Vacuum Pyrolysis hour (hours)

Irradiation with light

1 &Hexadienyl Hexamethylphosphoramide (Me3N)3P=O Hexamethylphosphorous triamide (Me3N)3P Isopropyl -CH(CH3)2 Lithium cyclohexylisopropylamide

Lithium diisopropylamide LiN(iPr)2 Lithium hexamethyl disilazide LiN(SiMe3)2 Lithium 2,2,6,6-tetramethylpiperidide

Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide) bis-(2,6-di-t-butyl-4-methylphenoxy)methyl aluminum meta-Chloroperoxybenzoic acid

Nicotinamide adenine dinucleotide Sodium triphosphopyridine nucleotide Napthy CC 1 oH$

Norbornadiene N-Bromosuccinimide N-Chlorosuccinimide N-Iodosuccinimide Raney nickel N-Methyl-2-pyrrolidinone

2 KHS05.KHS04aK2S04 Polymeric backbone

MeOCH2- CH3SO2- CH3SCH2-

Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol Phenyl

Benzene Toluene Phthaloyl 2-Pyridinecarboxylate

to \/

Piperidine 4-methoxyphenyl

[(MeOCH2CH20)2AlH2]Na set-Butyl CH3CH2CH(CH3) set-Butyllithium CH3CH2CH(Li)CH3 Diisoamyl (CH3)2CHCH(CH3)- a,a,a’,a’-tetraaryl-4,5-dimethoxy-1,3-dioxolane

tris-(Diethylamino)sulfonium difluorotrimethyl silicate Tetrabutylammonium fluoride n-Bu4N+F t-Butyldimethylsilyl t-BuMe2Si

J

TBHP (t-BuOOH) t-Butylhydroperoxide Me3COOH t-Bu tert-B utyl -C(CH3)3

Tetrahydrofuran Tetrahydropyran Tetramethylethylenediamine 1,1,3,3-Tetramethylguanidine Trimethylsilyl

2,2,6,6-Tetramethylpiperidine tetra-n-Propylammonium perruthenate Tolyl

Trityl Triisopropylphenylsulfonyl Tosyl = p-Toluenesulfonyl Sonication

Chiral auxiliary

CF3COOH (CF3CO)20 -S02CF3(-OS02CF3)

Me2NCH2CH2NMe2 -Si(CH3)3

4-c#&H3 -CPh3 4-Mec6&

INDEX, MONOFUNCTIONAL COMPOUNDS

Sections heavy type

Pages light type

Blanks in the table

correspond to sections

for which no additional

examples were found in

the literature

Sect Pg

Carboxylic acids 30A 9

Alcohols, phenols 45A

212 216 217 217 219 220 220 220 221 221 223 223 225

211 212 213 217 218 219 220 221 222 223 234 225

227 227 227 228 228 228 232 232 232 233 233 233

INDEX, DIFUNCTIONAL COMPOUNDS

Sections-heavy type

Pages-light type

Blanks in the table

correspond to sections

for which no additional

examples wem found in

INTRODUCTION

updating the 10650 in Volumes l-8 Volume 9 contains about 800 examples

tional groups Reviews have long been a feature of this series and Volume 9 adds almost 90 pertinent reviews in the various sections Volume 9 contains

previous edition Whether this represents a trend in the literature or an inad-

this

name, initials) The authors for each citation appear below the reaction The

as in Volumes 7 and 8

tions on the basis of the functional group of the starting material Within each

xvi INTRODUCTION

Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from methylenes Ketones from ketones Alkyls from alkenes (Hydrogenation of Alkenes) Alkynes from halides; also

al kynes from al kynes Esters from alcohols; also esters from carboxylic acids

Alkyls from alkenes (Conjugate Reduction) Alkyls from alkenes (Conjugate Rduction)

How to Use the Book to Locate Examples of the Preparation of Protection

of Monofunctional Compounds Examples of the preparation of one func-

ples of the reactions of a functional group are found in the horizontal rows of

transposition are found in Sections 1, 17, 33, and so on, lying close to a diag-

INTRODUCTION xvii

330 (Alcohol, Thiol-Ketone)

tecting group: reactions are located at the end of pertinent chapters

tions, although this is occasionally stated in the citation This is only done in cases where such generality is stated clearly in the original citation A reac- tion given in this book for a primary aliphatic substrate may also be applica-

imental conditions or precautions and the reader is referred to the original lit-

this book be taken as a complete experimental procedure Failure to refer to the original literature prior to beginning laboratory work could

be hazardous The original papers usually yield a further set of references

Classification and Organization of Reactions Forming Difunctional Compounds This chapter considers all possible difunctional compounds

tions on the basis of two functional grups in the product that are pertinent to the reaction The relative positions of the groups do not affect the classifica-

XVIII INTRODUCTION

ples illustrate applications of this classification system:

Halide-Halide Halide-Halide Alcohol-Ester Alcohol-Ester Ester-Alkene Ester-Alkene Alcohol-Ether Alcohol-Oxide

reaction was found In such cases both sections should be consulted

choice is dictated by the paper where the reaction was found

ing on the focus of the original paper

INTRODUCTION xix

account for roughly 60% of all the citations in Volume 9 This book was not

Engl.; Bull Chim Sot Be/g.; Bull Chim Sot Fr.; Can J Chem.; Chem

Chem Sot; Liebigs Ann Chem.; Org Prep Proceed Int.; Reel Tram Chim.,

Compendium of Organic Synthetic Methods

80%

Murakami M,; Hayashi, M.; Ito YJynlett, 1994, 179

Ph E Ph , toluene 5% MO(C0)6 , llO°C , 2o”c AcO(H2C)4 4-chlorophenol AcO(H2C)4

Review,” Rossi R,; Carpita, A.; Bellina, F Org Prep Proceed Znt., 1995, 27, 129

SECTION 2: ALKYNES FROM A4CID DERIVATIVES

Compendium of Organic Synthetic Methods, Volume 9 Michael B Smith

Copyright2001 by John Wiley & Sons, Inc.ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

Compendium of Organic Synthetic Methods, Vol9 Section 10

Bleicher, L.; Cosfwd N.D.P, Synlett, 1995, 111 5

Section 15 Alkynes from Misc

SECTION 11: ALKYNES FROM HYDRIDES

For examples of the reaction RC=CH + R&C-C=CR1, see section 300

0 TMSC(Li)Nz, THF

* P-Me -78OC + reflux 58%

Me

Miwa, K.; Aoyama T.: Shioiri, T, Synlett, 1994, 107

SECTION 13: ALKYNES FROM NITRILES

NO ADDITIONAL EXAMPLES

SECTION 14: ALKYNES FROM ALKENES

NaHMDS , THF -100°C V

OSiPhzt-Bu 98% Grandjean, D.; Pale, P.; Chuche, J Tetrahedron L&t., 1994, 35, 3529

SECTION 15: ALKYNES FROM MISCELLANEOUS COMPOUNDS

FVP (750°C)

w =t-Bu t-Bu

82%

Aitken R,A,; Atherton, J.I J Chem Sot., Per-kin Trans l., 1994, 128 1

From arylC0 derivatives:

A&ken R.A.; Horsburgh, C.E.R.; McCreadie, J.G.; Seth, S J Chem Sot., Perkin Trans l.,

1994, 1727

4 Compendium of Organic Synthetic Methods, Vo19 Section 15A

SECTION 15A: PROTECTION OF ALKYNES

NO ADDITIONAL EXAMPLB

Section 17 Acids from Acids

CHAPTER 2

PREPARATION OF ACID DERIVATIVES

SECTION 16: ACID DERIVATIVES FROM ALKYNES

Me0

(10 1) 82%

Kusumoto.T.; Ichikawa, S.; Asaka, K.; Sato, K.; Hiyama, T Tekhedron Lett., 1995, 36, 1071

0 C02H KF , microwave, 4 min

- ti

0 C02H OAc

<

94% O

Villemin D,; Labiad, B.; Loupy, A Synth Commun., 1993, 23, 419

Compendium of Organic Synthetic Methods, Volume 9 Michael B Smith

Copyright2001 by John Wiley & Sons, Inc.ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

6 Compendium of Organic Synthetic Methods, Vo19 Section 22

SECTION 18: ACID DERIVATIVES FROM ALCOHOLS AND

THIOLS

w llCH20H

02, Pb(OAc)p3 H@ , Pd-C , lh

w NaOH , H20,15O*C

Kirihara, M.; Yokoyama, S.; Kakuda, H.; Momose T, Tetrahedron Lett., 1995, 36,6907

SECTION 19: ACID DERIVATIVES FROM ALDEHYDES

NaN3-MnO$SiC14, CH$$ , O*C 0

89% N3

Elmorsv SS Tetrahedron Lett., 1995, 36, 1341

SECTION 20: ACID DERIVATIVES FROM ALKYLS,

METHYLENES AND ARYLS

Section 25 Acids from Halides

SECTION 23: ACID DERIVATIVES FROM ESTERS

Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids)

CO (3 atm) ,8% PPh3 PhMOCHO

96h, rt

* PhMCOzH

92% (E only) mote 4 Bull Chem Sot Jpn., 1995, 68, 433

SECTION 24: ACID DERIVATIVES FROM ETHERS,

EPOXIDES AND THIOETHERS

Ph

1 10% [Bi(mandelate)&O DMSO , 80°C ,30 min, air

2 H30+

Zevaco, T.; Dufiach, E.; Postel M, Tetrahedron Lett., 1993, 34, 2601

C02H AgBQ , AlC13 , MeCN

reflux ,0.35h

95%

SECTION 25: ACID DERIVATIVES FROM HALIDES AND

SULFONATES

C02, H2, 150°C, Id

Ni(cod)2 + C%(C0)8 muoka A; Gotoh, N.; Kobayashi, N.; Hirano, M.; I(omiva S, Chem Lett., 1995, 567

Compendium of Organic Synthetic Methods, Vo19 Section 29

SECTION 28: ACID DERIVATIVES FROM NITRILES

NO ADDITIONAL EXAMPLES

SECTION 29: ACID DERIVATIVES FROM ALKENES

Fe(CO)5, KOH , CO (1 atm)

Section 30A Protection of Acids

C6H13 cat 0~04, Jones reagent

\

* C6H13-C02H acetone, rt

Henry, J.R.; Webeb S pvt J Org Chem., 1993, 58, 4745

SECTION 30: ACID DERIVATIVES FROM MISCELLANEOUS

COMPOUNDS

PhI02

1 0.1% Na2[PdC14] , CO , Hz0 Nag03 , 40°C ,6.5h

* PhCOOH 71%

2 H30+

Grushin, V.V.; Alter H, J Org Chem., 1993, 58, 4794

SECTION 30A: PROTECTION OF CARBOXYLIC ACID

acidic Al203 ,7 min C02H QPh microwave , CH2C12, rt 92%

0

Yanna R&; Chatterjee, AK; Varma, M, Tetrahedron Lett., 1993, 34,4603

10 Compendium of Organic Synthetic Methods, Vol9 Section 30A

P COzH

12, cyclohexane , rt cossV,; Albouy, A.; Scheloske, M.; Gomez Pardo, D Tetrahedron L&t., 1994, 3.5, 1539

1% TFA in CH2C12 ,5 min , rt ematowicz, MS,; Chao, H.-G.; Matsueda, G.R Tetrahedron Lett., 1994, 35, 1651

CuC12, 02, aq DMF

phod ph 1 Ph-C02H

45% -R.N.; Singh, L Tetrahedron Lett., 1995, 36, 5401

1 NBS, (Bz0)2, CC14 , heat Tco2Bn 2 H20 - r3:“”

m M&; Montana, J.G Synlett, 1994, 219

REVIEW:

“Recent Developments in Chemical Deprotection of Ester Functional Groups,” Salomon, C.J.; Mata, E.G.; Mascaretti, O.A Tetrahedron, 1993, 49, 3691

Other reactions useful for the protection of carboxylic acids are included in

Section 107 (Esters from Carboxylic Acids and Acid Halides) and Section 23 (Carboxylic Acids from Esters)

Section 32 Alcohols from Acids 11

SECTION 32: ALCOHOLS AND THIOLS FROM ACID

Narasimhan S.; Madhavan, S.; Prasad, KG J Org Chem., 1995, 60, 53 14

Barton, D.H.R.; Castagnino, E,; Jaszberenyi, J.Cs Tetrahedron Lett., 1994, 35, 6057

Compendium of Organic Synthetic Methods, Volume 9 Michael B Smith

Copyright2001 by John Wiley & Sons, Inc.ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

12 Compendium of Organic Synthetic Methods, Vol9 Section 33

SmIrH20,l min PhCO2H

SECTION 33: ALCOHOLS AND THIOLS FROM ALCOHOLS

AND THIOLS

Lawesson’s reagent , toluene

o T, J Chem Sot., Perkin Trans I., 1993, 1113

MeO-{=)+OH “‘EyF * MeO-(=)-OH g3% Kabalka GW,; Reddy, N.K.; Narayana, C Tetrahedron Lett., 1993, 34, 7667

K Geo trichium candidum immobilized OH

with a water-adsorbent polymer

Ph hexane * A

+

89%ee,R (56 w Nakamura.; Inoue, Y.; Ohno, A Tetrahedron Lett., 1994, 35,4375

Section 34A Reduction of Aldehydes to Alcohols 13

SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES

The following reaction types are included in this section:

A Reductions of Aldehydes to Alcohols

B Alkylation of Aldehydes, forming Alcohols

Coupling of Aldehydes to form Diols is found in Section 323 (Alcohol-Alcohol)

74%

amazaki S, Chem Lett., 1995, 127

SECTION 34A: REDUCTIONS OF ALDEHYDES TO ALCOHOLS

14 Compendium of Organic Synthetic Methods, Vo19 Section 34B

Bu$nH , SiO2, rt CHO CH2C12, Id

81%

&g&&&; Chaboche, C.; Franck, X.; Peyrat, J.-F .I Org Chem., 1995, 60, 7138 REVIEW:

“P-Hydroxy Diisopinocampheylborane As A Mild, Chemoselective Reducing Agent For Aldehydes,” Cha.; Kim, E.J.; Kwon, 0.0.; Kwon, S.Y.; Seo, W.W.; Chang, S.W Org Prep Proceed Int., 1995, 27, 541

SECTION 34B: ALKYLATION OF ALDEHYDES, FORMING

ALCOHOLS ASYMMETRIC ALKYLATIONS

Bn-Cl

Et2Zn

* -IO

R-BJNOL$Ti(OiPr)4, MS 4A, TFA PhCHO

-20°C, 14h ,

95% (96% ee) Keck G&; Krishnamurthy, D.; Grier, M.C J Org Chem., 1993, 58, 6543

Section 36 Alcohols from Amides 15

96% (82% ee , S) Costa, A.L.; Piazza, M.G.; Tanliavini, E,; Trombini, C.; 1[ Jmani-Ronchi A, J Am Chem Sot.,

100% ee

With a chiral oxazoline additive, 60% ee

16 Compendium of Organic Synthetic Methods, Vol9 Section 34B

TTPWI NHTf

with Ti(OiPr)d - 80% yield, 0% ee Nowotng, S.; Vettel, S.; Mel, P, Tetrahedron Lett., 1994, 35, 4539

Section 36 Alcohols from Amides 17

Keck G.E,; Krishnamurthy, D.; Chen, X Tetrahedron Lett., 1994, 35, 8323

18 Compendium of Organic Synthetic Methods, Vol9 Section 34B

PhCHO

) 10%

00 ~111 CH (Mes)OLi

Ph

N

Et$n , chiral ferrocene catalyst PhCHO

Bedeschi, P.; Casolari, S.; Costa, A.L.; Tagliavini, E,; Umani-Ronchi, A Tetrahedron Lett.,

1995, 36, 7897

1 chiral Ti complex , ether

* 2TFA,THF

OTMS

pi0

97% (80% ee) Singer, R.A.; &reira E.M, J Am Chem Sot., 1995, 117, 12360

Section 36 Alcohols from Amides 19

PhCHO , Et$n , THF cat Pd(PPh& , rt ,3h H

- JJ

I

88% Yasui, K.; Goto, Y.; Yajima, T.; Taniseki, Y.; Fugami, K.; Tanaka, A.; Tamaru Y, Tetrahedron Lett., 1993, 34, 7619

5% Ir(CO)(PPh&C104, 30h Nuss J.M,; Rennels, R.A Chem Lett., 1993, 197

83%

PhCHO

1 e I , SnC12.2 Hz0

* NaI,DMF ,hL

2,30%NH4F,H20

89%

Imai, T,; Nishida, S Synthesis, 1993, 395

20 Compendium of Organic Synthetic Methods, Vo19 Section 34B

PhBCHO

1 Bu$nSiMe3, THF, rt 3h,Bu@CN

Masaya, K.; Tanino, K.; Kuwajima I, Tetrahedron Lett., 1994, 35, 7965

BuGn-noMe :.I::b’” * -780zpJ-JoMe

90% (70:30 de) Colombo L,; DiGiacomo, M.; Brusotti, G.; Delougu, G Tetrahedron Lett., 1994, 35, 2063

Section 36 Alcohols from Amides 21

*3

4

SiMQ

l.Ga,KI,LiCl PhCHO , TI-IF , reflux

Ph 9) 95%

EtCHO , Zn , aq NH&I, THF

Clayden, J.; lulia.M, J Chem Sot Chem Commun., 1994, 1905

22 Compendium of Organic Synthetic Methods, Vol9 Section 34B

2.2 Et2Zn , CgHlgCHO THF , reflux Clayden JJ Julia, M J Chem Sot Chem Commun., 1994,226l

PhCHzSiMe3 , hv , MeCN Mg(C104)2, 6.5h