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Asymmetric Synthesis of Alkyl Aziridine‐2‐Carboxylates from Chiral 3′‐Benzyloxy‐aminoimides
Author(s) -
Cardillo Giuliana,
Casolari Sonia,
Gentilucci Luca,
Tomasini Claudia
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199618481
Subject(s) - aziridine , alkyl , lithium (medication) , enantioselective synthesis , chemistry , combinatorial chemistry , catalysis , medicinal chemistry , stereochemistry , materials science , organic chemistry , psychology , ring (chemistry) , psychiatry
Diastereoselectivities at previously unattained levels. Aziridines 2 can be prepared from precursors 1 via the Ti or Al enolates in > 99% de . Further advantages of this approach are the easy access to 1 by AlMe 2 Cl‐catalyzed 1,4‐addition of O ‐benzylhydroxylamine to α,β‐unsaturated chiral imides, and the straightforward recovery of the chiral auxiliary by treatment with lithium benzyloxide. R = Me, Et, n Pr; M = TiCl 4 , AlMe 2 Cl.