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A Valuable Synthetic Route to the Enantiopure Functionalized N ‐Substituted Aziridines
Author(s) -
Li SenLan,
Guo JinBo,
Yu ZhaoUan,
Chen QingHua
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040220413
Subject(s) - enantiopure drug , chemistry , combinatorial chemistry , molecule , organic chemistry , stereochemistry , enantioselective synthesis , catalysis
Chiral butyrolacto[3,4‐ b ]‐2(S)‐6( R )‐l‐N‐alkylaziridines 7 were synthesized in enantiopure form utilizing racemic 5‐methoxy‐3‐bromo‐2(5 H )furanone (5) and available amines (6) as key precursors. After highly effective reduction of 7, the functionalized 2( S ),3( R )‐dihydroxymethyl‐ N ‐alkylaziridines (8) were obtained in good yields with ≥98% ee . This is a simple and practical method for the preparation of enantiopure aziridines which are important intermediates in the synthesis of biologic active molecules.