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OPTICALLY-ACTIVE AMINOALCOHOL PROMOTED ADDITION OF 2-PYRIDYLTHIOESTER BORON ENOLATES TO IMINES - ENANTIOSELECTIVE ONE-POT SYNTHESIS OF BETA-LACTAMS

被引：20
作者：
ANNUNZIATA, R
BENAGLIA, M
CINQUINI, M
COZZI, F
MOLTENI, V
RAIMONDI, L
机构：
[1] UNIV MILAN,CTR CNR,I-20133 MILAN,ITALY
[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
来源：
TETRAHEDRON | 1995年 / 51卷 / 32期
关键词：
D O I：
10.1016/0040-4020(95)00503-Z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.
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收藏
页码：8941 / 8952
页数：12
相关论文
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