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Lithiation of Cinnamyl Chloride: Stereoselective Synthesis of Propargylic Oxiranes and Aziridines
Author(s) -
Florio Saverio,
Troisi Luigino,
Capriati Vito,
Suppa Giovanna
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200011)2000:22<3793::aid-ejoc3793>3.0.co;2-m
Subject(s) - chemistry , stereoselectivity , chloride , organic chemistry , alkylation , halo , medicinal chemistry , catalysis , physics , quantum mechanics , galaxy
Propargylic oxiranes 4a − e and aziridines 8a − c have been prepared from cinnamyl chloride through lithiation−alkylation with α‐halo carbonyl compounds and α‐chloro imines, respectively. The reaction with substituted α‐halo carbonyl compounds and α‐chloro imines proved to be highly E diastereoselective.