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One‐Pot Synthesis of Chiral Aziridines by a Domino Reaction by Using Desulfonylative Formation on the N ‐Tosyl Imine of Chloroacetaldehyde with an Asymmetric Mannich Reaction as a Key Step
Author(s) -
Hayashi Yujiro,
Urushima Tatsuya,
Sakamoto Daisuke,
Torii Kou,
Ishikawa Hayato
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101668
Subject(s) - aziridine , tosyl , imine , chemistry , silylation , combinatorial chemistry , domino , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis , ring (chemistry)
Aziridines with ease : A one‐pot synthesis of chiral aziridine derivatives with excellent diastereo‐ and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N ‐Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).