New carbohydrate-based chiral auxiliaries in Diels-Alder reaction

被引：20

作者：

Ferreira, MLG

Pinheiro, S

Perrone, CC

Costa, PRR

Ferreira, VF ^{[1
]}

机构：

[1] Univ Fed Fluminense, GQO, Inst Quim, CEG Ctr, BR-24210150 Niteroi, RJ, Brazil

[2] Inst Nacl Tecnol, BR-20081380 Rio De Janeiro, Brazil

[3] Univ Fed Rio de Janeiro, CCS, BR-21941590 Rio De Janeiro, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(98)00286-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The carbohydrate derivatives 1-5 were evaluated as chiral auxiliaries in the Diels-Alder reaction of its acrylate derivatives 6a-e with cyclopentadiene promoted by Lewis acids. Although excellent endo:exo ratios (98:2) were obtained in many cases, the rr-facial selectivities were from low to moderate (up to 60% d.e.). An effect of noncoordinating solvents reversing the stereoselectivities of adducts obtained from acrylates 6a,b was also found. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2671 / 2680

页数：10

共 29 条

[21] SYNTHESIS OF 1,4,5-TRI-O-BENZOYL-2,3-DIDEOXY-D-ERYTHRO-HEX-2-ENULOPYRANOSE DERIVATIVE OF A KETOSE-RELATED GLYCAL HAVING AN ENDOCYCLIC DOUBLE BOND [J].