KINETIC RESOLUTION OF THE ACROLEIN DIMER BY ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS

被引：28

作者：

REIN, T ^{[1
]}

KANN, N ^{[1
]}

KREUDER, R ^{[1
]}

GANGLOFF, B ^{[1
]}

REISER, O ^{[1
]}

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 05期

关键词：

D O I：

10.1002/anie.199405561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diastereoselectivities up to 98% de have been reached in kinetic resolutions of the racemic acrolein dimer 1 by reaction with the chiral phosphonates 2. Depending on the choice of substituents on the phosphoryl group (R  CF3CH2, C2H5), either (E)‐3 or (Z)‐3, both of which are versatile synthetic building blocks, can be obtained as the major product. The dominant isomer for (Z)‐3 is the (S) isomer and for (E)‐3 the (R) isomer. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：556 / 558

页数：3

共 15 条

[1] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[2]

FOURIE RW, 1962, ACROLEIN, P181

[3] SYNTHESIS OF OPTICALLY-ACTIVE 3-OXA-CARBACYCLIN PRECURSORS FEATURING ASYMMETRIC HORNER-EMMONS REACTION [J].

GAIS, HJ ;

SCHMIEDL, G ;

BALL, WA ;

BUND, J ;

HELLMANN, G ;

ERDELMEIER, I .

TETRAHEDRON LETTERS, 1988, 29 (15) :1773-1774

[4] STUDIES IN ASYMMETRIC OLEFINATIONS - THE SYNTHESIS OF ENANTIOMERICALLY PURE ALLYLIDENE, ALKYLIDENE, AND BENZYLIDENE CYCLOHEXANES [J].

HANESSIAN, S ;

BEAUDOIN, S .

TETRAHEDRON LETTERS, 1992, 33 (50) :7655-7658

[5] EFFICIENT ESTER EXCHANGE-REACTION OF PHOSPHONOACETATES [J].

HATAKEYAMA, S ;

SATOH, K ;

SAKURAI, K ;

TAKANO, S .

TETRAHEDRON LETTERS, 1987, 28 (24) :2713-2716

[6] OZONOLYSIS OF CYCLIC ENOL ETHERS - AN EFFICIENT STRATEGY TO ALDOL AND HOMOALDOL COMPOUNDS [J].

HILLERS, S ;

NIKLAUS, A ;

REISER, O .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3169-3171

[7] KETONE METHYLENATION WITH OPTICAL RESOLUTION - SYNTHESIS OF (+)-HOP AND (-)-HOP ETHER [J].

JOHNSON, CR ;

ELLIOTT, RC ;

MEANWELL, NA .

TETRAHEDRON LETTERS, 1982, 23 (48) :5005-5008

[8] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES [J].

KANN, N ;

REIN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3802-3804

[9]

Kelly S. E., 1991, COMPREHENSIVE ORGANI, V1, P761

[10] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].

MARYANOFF, BE ;

REITZ, AB .

CHEMICAL REVIEWS, 1989, 89 (04) :863-927

← 1 2 →