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
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.
引用
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页码:1349 / 1352
页数:4
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