HIGHLY STEREODIVERGENT APPROACH TO BOTH ENANTIOMERS OF 4-SUBSTITUTED BETA-LACTAMS VIA DIASTEREOFACIALLY CONTROLLED ADDITION OF ENOLATES OF TERT-BUTYL ACETATE TO A CHIRAL IMINE

被引：20

作者：

SHIMIZU, M ^{[1
]}

UKAJI, Y ^{[1
]}

TANIZAKI, J ^{[1
]}

FUJISAWA, T ^{[1
]}

机构：

[1] MIE UNIV, DEPT CHEM MAT, TSU, MIE 514, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 07期

关键词：

D O I：

10.1246/cl.1992.1349

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Addition of lithium or triisopropoxytitanium enolate derived from t-butyl acetate to a chiral imine possessing dioxolane ring as a chiral auxiliary gave (3S)-beta-amino ester exclusively, whereas chlorozinc enolate underwent re-facial attack to give (3R)-isomer with good selectivity. The beta-amino esters thus obtained were readily converted to the corresponding (4S)- and (4R)-beta-lactams respectively without loss of the stereochemical integrity at C-4 of the beta-lactam rings.

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页码：1349 / 1352

页数：4

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