2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose as chiral auxiliary in asymmetric alpha-alkylation of ester enolates

被引：12

作者：

Costa, PRR

Ferreira, VF

Alencar, KG

Filho, HCA

Ferreira, CM

Pinheiro, S

机构：

[1] UNIV FED RIO DE JANEIRO,BR-21941 RIO JANEIRO,BRAZIL

[2] UNIV FED FLUMINENSE,DEPT QUIM ORGAN,BR-24210150 NITEROI,RJ,BRAZIL

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1996年 / 15卷 / 06期

关键词：

D O I：

10.1080/07328309608005685

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The asymmetric alpha-alkylation of enolates of chiral esters derived from 2,3:4,5-di-O-isopropylidene-beta--D-fructopyranose (1) was studied. The diastereoselectivities range from 1:1 to 7:3. The absolute stereochemistry of the major S-isomers were established by chemical correlation. The diastereoselectivities of the alkylated products were similar to those observed in the deprotonation steps. The stereochemical outcome can be interpreted by an intramolecular complexation of the lithium cation of the carbohydrate ester enolates.

引用

页码：691 / 699

页数：9

共 12 条

[1]

EVANS DA, 1984, ASYMMETRIC SYNTHES B, V3, P213

[2]

Hanessian S., 1983, Total Synthesis of Natural Products: The Chiron Approach

[3] ACYCLIC STEREOSELECTION .11. DOUBLE STEREO-DIFFERENTIATION AS A METHOD FOR ACHIEVING SUPERIOR CRAMS RULE SELECTIVITY IN ALDOL CONDENSATIONS WITH CHIRAL ALDEHYDES [J].