SYNTHESIS OF E-VINYL AND Z-VINYL ETHERS BY THE HORNER-WITTIG REACTION

被引：131

作者：

EARNSHAW, C ^{[1
]}

WALLIS, CJ ^{[1
]}

WARREN, S ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 12期

关键词：

D O I：

10.1039/p19790003099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diphenyl(methoxymethyl)- and diphenyl-(1-methoxyethyl)-phosphine oxides form lithium derivatives which add to aldehydes and ketones. The adducts may be separated into crystalline diastereoisomers each giving a single geometrical isomer of a vinyl ether on treatment with base. Hydrolysis of the vinyl ethers provides a reliable aldehyde synthesis in which the lithium derivative (19) behaves as a formyl anion equivalent. The method has been used to convert an acyl indole into a vinyl ether in compounds related to the strychnos alkaloids.

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页码：3099 / 3106

页数：8

相关论文

共 63 条

[1] ALPHA-METHOXYVINYLLITHIUM AND RELATED METALATED ENOL ETHERS - PRACTICAL REAGENTS FOR NUCLEOPHILIC ACYLATION [J].

BALDWIN, JE ;

HOFLE, GA ;

LEVER, OW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7125-7127

[2] CONVENIENT ROUTE TO DIHYDROXYACETONE SUBSTITUENT [J].

BALDWIN, JE ;

LEVER, OW ;

TZODIKOV, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (13) :2312-2314

[3] ACYL ANION EQUIVALENTS - 2 SIMPLE AND VERSATILE KETONE SYNTHESES [J].

BLATCHER, P ;

GRAYSON, JI ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (14) :547-549

[4] CARBON ACIDS .9. EFFECTS OF DIVALENT SULFUR AND DIVALENT OXYGEN ON CARBANION STABILITIES [J].

BORDWELL, FG ;

VANDERPUY, M ;

VANIER, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1885-1886

[5] PREPARATIVE METHODS FOR BETA-ACYL VINYL ANION EQUIVALENTS FROM ENONES OR ALLYL SULFIDES [J].

COHEN, T ;

BENNETT, DA ;

MURA, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2506-2507

[6] NEW SYNTHESIS OF ALPHA,BETA-UNSATURATED ALDEHYDES USING 1,3-BIS(METHYLTHIO)ALLYLLITHIUM [J].

COREY, EJ ;

ERICKSON, BW ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1724-&

[7] A METHOD FOR INTRODUCTION OF 2 CARBON APPENDAGES AT A CARBONYL CARBON - APPLICATION TO DOUBLE CHAIN BRANCHING AND SPIRO ANNULATION OPERATIONS [J].

COREY, EJ ;

SHULMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5522-&

[8]

COULSON DR, 1964, TETRAHEDRON LETT, P3323

[9]

Daufresne M, 1907, CR HEBD ACAD SCI, V145, P875

[10]

DAUFRESNE M, 1908, J CHEM SOC A, P19

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