A SUPERIOR CHIRAL AUXILIARY IN ALDOL CONDENSATIONS - CAMPHOR-BASED OXAZOLIDONE

被引：20

作者：

YAN, TH

CHU, VV

LIN, TC

TSENG, WH

CHENG, TW

机构：

[1] Department of Chemistry, National Chung-Hsing University

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 40期

关键词：

D O I：

10.1016/0040-4039(91)80084-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol reactions from boron enolate derived from camphor-based N-propionyloxazolidone exhibit exceptionally high stereoselection. The initial aldol adducts from lithium mediated reactions equilibrate to furnish erythro isomers. Erythro selection is controlled by the choice of the enolate counterion.

引用

收藏

页码：5563 / 5566

页数：4

相关论文

共 33 条

[21] ASYMMETRIC ALPHA-ACETOXYLATION OF CARBOXYLIC ESTERS [J].

OPPOLZER, W ;

DUDFIELD, P .

HELVETICA CHIMICA ACTA, 1985, 68 (01) :216-219

[22] CAMPHORSULFONAMIDE-SHIELDED, ASYMMETRIC 1,4-ADDITIONS AND ENOLATE ALKYLATIONS - SYNTHESIS OF A SOUTHERN CORN-ROOTWORM PHEROMONE [J].

OPPOLZER, W ;

DUDFIELD, P ;

STEVENSON, T ;

GODEL, T .

HELVETICA CHIMICA ACTA, 1985, 68 (01) :212-215

[23] ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF N-ACYL-CAMPHOR-SULTAM TRIENES [J].

OPPOLZER, W ;

DUPUIS, D .

TETRAHEDRON LETTERS, 1985, 26 (44) :5437-5440

[24] BORNANESULTAM-DIRECTED ASYMMETRIC-SYNTHESIS OF CRYSTALLINE, ENANTIOMERICALLY PURE SYN ALDOLS [J].

OPPOLZER, W ;

BLAGG, J ;

RODRIGUEZ, I ;

WALTHER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2767-2772

[25] ASYMMETRIC SYNTHESES OF ALPHA-AMINO-ACIDS FROM ALPHA-HALOGENATED 10-SULFONAMIDO-ISOBORNYL ESTERS [J].

OPPOLZER, W ;

PEDROSA, R ;

MORETTI, R .

TETRAHEDRON LETTERS, 1986, 27 (07) :831-834

[26] EFFICIENT ASYMMETRIC HYDROGENATIONS OF CAMPHOR-SULTAM-IMIDE-CONJUGATED ALKENES [J].

OPPOLZER, W ;

MILLS, RJ ;

REGLIER, M .

TETRAHEDRON LETTERS, 1986, 27 (02) :183-186

[27] CAMPHOR-DERIVED N-ACRYLOYL AND N-CROTONOYL SULTAMS - PRACTICAL ACTIVATED DIENOPHILES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].

OPPOLZER, W ;

CHAPUIS, C ;

BERNARDINELLI, G .

HELVETICA CHIMICA ACTA, 1984, 67 (05) :1397-1401

[28] ASYMMETRIC DIELS-ALDER AND ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

OPPOLZER, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :876-889

[29]

OPPOLZER W, 1985, TETRAHEDRON LETT, V26, P5037

[30] MECHANISTIC IMPLICATIONS OF THE TETRAMERIC CUBIC STRUCTURE OF LITHIUM ENOLATES [J].

SEEBACH, D ;

AMSTUTZ, R ;

DUNITZ, JD .

HELVETICA CHIMICA ACTA, 1981, 64 (08) :2622-2626

← 1 2 3 4 →