LICLO4-CATALYZED NUCLEOPHILIC-ADDITION TO ALPHA-CHIRAL ALDEHYDES, ALDIMINES, AND OXIRANES

被引：41

作者：

IPAKTSCHI, J

HEYDARI, A

机构：

[1] Institut Für Organische Chemie, Universität Gießen, Gießen, D-35392

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 08期

关键词：

KETENE ACETALS; O-SILYLATED; ALDEHYDES; ALPHA-ALKOXY; ALPHA-AMINO ALDEHYDES; MUKAIYAMA ALDOL REACTIONS; CYANHYDRINES; ALDIMINES; BETA-AMINO ESTERS; DIASTEREOSELECTIVITY; OXIRANES; RING OPENING;

D O I：

10.1002/cber.19931260822

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The diastereoselectivity of lithium perchlorate-induced addition of trimethylsilyl cyanide and O-silylated ketene acetals to alpha-chiral aldehydes is studied. Whereas aldehyde 1 reacts with the ketene acetal 2 exclusively to form the syn-ester 3, a divergent selectivity is observed in the case of trimethylsilyl cyanide addition to 5 and 11a-c. Also the reaction of O-silylated ketene acetals with aldimines 16 in the presence of lithium perchlorate proceeds smoothly to afford the corresponding beta-amino esters 17 in high yields. While the silyl ketene acetal of methyl acetate leads preferentially to the corresponding anti-diastereomer, in the case of the silyl ketene acetal of methyl isobutyrate a syn-/anti-selectivity in the range of 79:21 to 44:56 is observed. In the presence of lithium perchlorate solution in ether the oxiranes 27a-d undergo facile nucleophilic ring opening reactions with 2, 29, and 30.

引用

页码：1905 / 1912

页数：8

共 52 条

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