Asymmetric Synthesis of Alkyl Aziridine‐2‐Carboxylates from Chiral 3′‐Benzyloxy‐aminoimides | Zendy

Cardillo Giuliana | Zendy; Casolari Sonia | Zendy; Gentilucci Luca | Zendy; Tomasini Claudia | Zendy

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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.

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