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A Convenient, Room‐Temperature–Organic Base Protocol for Preparing Chiral 3‐(Enoyl)‐1,3‐oxazolidin‐2‐ones
Author(s) -
Soloshonok Vadim A.,
Ueki Hisanori,
Jiang Changchun,
Cai Chaozhong,
Hruby Victor J.
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3616::aid-hlca3616>3.0.co;2-o
Subject(s) - chemistry , steric effects , base (topology) , combinatorial chemistry , simplicity , protocol (science) , reaction conditions , simple (philosophy) , organic base , organic chemistry , catalysis , medicine , mathematical analysis , philosophy , alternative medicine , mathematics , epistemology , pathology
In this study, we developed a new protocol for the preparation of the chiral 3‐[( E )‐enoyl]‐1,3‐oxazolidin‐2‐ones under the ultimately simple reaction conditions starting with the corresponding enoyl chlorides and 1,3‐oxazolidin‐2‐ones with Et 3 N/LiCl at room temperature. The method generally allows efficient preparation of various derivatives regardless of the steric and electronic nature of the substituents on both the enoyl or the oxazolidinone sites. Excellent yields, combined with the simplicity of the experimental procedures, render the present method immediately useful for preparing the target compounds.