STEREOSELECTIVE HYDRIDE REDUCTIONS OF CHIRAL 2-P-TOLYLSULFINYLCYCLOALKANONES

被引：16

作者：

BUENO, AB

CARRENO, M

RUANO, JLG

PENA, B

RUBIO, A

HOYOS, MA

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM C-I,E-28049 MADRID,SPAIN

[2] UNIV AUTONOMA MADRID,DEPT QUIM AGR & GEOQUIM C-VI,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON | 1994年 / 50卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(01)85512-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly stereoselective hydride reductions of chiral 2-p-tolylsulfinyl-cyclopentanones and cycloheptanones are described. With DIBAL (electrophilic hydride) the configuration induced at C-1 is controlled by the sulfinyl group (1,3-asymmetric induction), and it can be inverted by using ZnCl2 as catalyst. With L-selectride the stereoselectivity is directed by the C-2 chiral groups (1,2-asymmetric induction). Other nucleophilic hydrides gave results which depend on the reagents and the size of the rings.

引用

页码：9355 / 9364

页数：10

共 19 条

[1]

BARROS D, 1992, TETRAHEDRON LETT, V33, P2733

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