THE STEREOSELECTIVE HORNER-WITTIG REACTION WITH PHOSPHINE OXIDES - SYNTHESIS OF HINDERED Z-ALKENES VIA LUCHE REDUCTION

被引：31

作者：

HUTTON, G ^{[1
]}

JOLLIFF, T ^{[1
]}

MITCHELL, H ^{[1
]}

WARREN, S ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 43期

关键词：

D O I：

10.1016/0040-4039(95)01629-V

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural anti selectivity of the Homer-Wittig reaction with phosphine oxides is reduced when there is a branched chain next to the new C=C double bond. A better approach is Luche reduction of the corresponding ketones which gives high anti selectivity when the branched chain is placed on the side chain next to the phosphine oxide.

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页码：7905 / 7908

页数：4

相关论文

共 23 条

[1] N-BOC 2-ACYLOXAZOLIDINES - USEFUL PRECURSORS TO ENANTIOPURE 1,2-DIOLS VIA HIGHLY DIASTEREOSELECTIVE NUCLEOPHILIC ADDITIONS [J].

AGAMI, C ;

COUTY, F ;

LEQUESNE, C .

TETRAHEDRON, 1995, 51 (14) :4043-4056

[2] STEREOCHEMICALLY CONTROLLED SYNTHESIS OF UNSATURATED ALCOHOLS BY THE HORNER-WITTIG REACTION [J].

AYREY, PM ;

BOLTON, MA ;

BUSS, AD ;

GREEVES, N ;

LEVIN, D ;

WALLACE, P ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3407-3417

[3] APPLICATIONS OF THE STEREOCHEMICALLY-CONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF FENICULIN, (E)-NON-6-EN-1-OL, A PHEROMONE OF THE MEDITERRANEAN FRUIT-FLY, (E)-DEC-5-EN-1-OL, AND (Z)-DEC-5-EN-1-OL, TRI-SUBSTITUTED ALKENES, AND (Z)-ALPHA-BISABOLENE [J].

BUSS, AD ;

GREEVES, N ;

MASON, R ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2569-2577

[4] THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES [J].

BUSS, AD ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2307-2325

[5] ALKENYL OXAZOLIDINONES BY STEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES - SYNTHESIS OF ANY ISOMER (RR, RS, SR OR SS, E OR Z) BEARING 1,4-RELATED CHIRAL CENTERS ACROSS A DOUBLE-BOND [J].

CLAYDEN, J ;

COLLINGTON, EW ;

LAMONT, RB ;

WARREN, S .

TETRAHEDRON LETTERS, 1993, 34 (13) :2203-2206

[6]

CLAYDEN J, IN PRESS ANGEW CHEM

[7]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[8] A NEW, GENERAL, AND STEREOSELECTIVE METHOD FOR THE SYNTHESIS OF TRISUBSTITUTED ALKENES [J].

DENMARK, SE ;

AMBURGEY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10386-10387

[9] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[10] STRUCTURE AND CONFORMATION OF ALPHA'-DIPHENYLPHOSPHINOYL ENONES - X-RAY STRUCTURE OF E-(5SR,6SR)-3,6-DIMETHYL-5-DIPHENYLPHOSPHINOYL-7-TRIPHENYLMETHOXYHEPT-2-EN-4-ONE [J].

DOYLE, MJ ;

HALL, D ;

RAITHBY, PR ;

SKELTON, N ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :517-523