THE SYNTHESIS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES BY PALLADIUM(II)-CATALYZED ALLYLIC ACETATE TRANSPOSITION

被引：12

作者：

CLAYDEN, J ^{[1
]}

WARREN, S ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 23期

关键词：

D O I：

10.1039/p19930002913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph2PO) group, is regiospecific (acetate moves away from the Ph2PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to delta-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.

引用

页码：2913 / 2923

页数：11

共 26 条

[1] STEREOCONTROLLED SYNTHESIS OF HOMOALLYLIC AMINES USING PHOSPHINE OXIDES AND ISOXAZOLINES
ARMSTRONG, SK
WARREN, S
COLLINGTON, EW
NAYLOR, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (33) : 4171 - 4174
[2] A NEW METHOD FOR STEREOSELECTIVE HOMOALLYLIC AMINE SYNTHESIS
ARMSTRONG, SK
COLLINGTON, EW
KNIGHT, JG
NAYLOR, A
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13): : 1433 - 1447
[3] EXTENSION OF THE HORNER-WITTIG REACTION TO THE SYNTHESIS OF E-ALKENES WITH CHIRAL SUBSTITUENTS - STEREOCHEMICAL CONTROL BY ACYL TRANSFER
AYREY, PM
WARREN, S
[J]. TETRAHEDRON LETTERS, 1989, 30 (34) : 4581 - 4584
[4] BABLER JH, 1974, TETRAHEDRON LETT, P351
[5] ANIONOTROPY
BRAUDE, EA
[J]. QUARTERLY REVIEWS, 1950, 4 (04): : 404 - 425
[6] BRAUDE EA, 1949, CHEM SOC ANN REP, P125
[7] TRANSPOSITION OF ALLYLIC ALCOHOLS CONTROLLED BY THE PH2PO GROUP - REAGENTS FOR ALPHA-HYDROXY-DIENE SYNTHESIS BY THE HORNER-WITTIG REACTION
BROWN, PS
MCELROY, AB
WARREN, S
[J]. TETRAHEDRON LETTERS, 1985, 26 (02) : 249 - 252
[8] THE SYNTHESIS OF (Z)-PENTA-2,4-DIEN-1-OL AND SUBSTITUTED (E)-PENTADIENOLS BY THE STEREOCHEMICALLY CONTROLLED HORNER-WITTIG REACTION
BROWN, PS
GREEVES, N
MCELROY, AB
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06): : 1485 - 1492
[9] THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES
BUSS, AD
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2307 - 2325
[10] STEREOCONTROLLED SYNTHESIS OF R OR S, E OR Z UNSATURATED ALPHA-AMINO-ACIDS BY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES
CLAYDEN, J
COLLINGTON, EW
WARREN, S
[J]. TETRAHEDRON LETTERS, 1993, 34 (08) : 1327 - 1330

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