Premium
Asymmetric Hydroazidation of Nitroalkenes Promoted by a Secondary Amine‐Thiourea Catalyst
Author(s) -
Bellavista Tiziana,
Meninno Sara,
Lattanzi Alessandra,
Della Sala Giorgio
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500403
Subject(s) - chemistry , thiourea , amine gas treating , catalysis , nitro , benzoic acid , organic chemistry , enantioselective synthesis , organocatalysis , optically active , medicinal chemistry , combinatorial chemistry , alkyl
Chiral β‐nitro azides are obtained by asymmetric addition of azides to nitroalkenes, with an enantioselectivity of up to 82% ee . The reaction, promoted by an easily accessible secondary amine‐thiourea catalyst, is performed with azidotrimethylsilane in the presence of benzoic acid. Products with different aliphatic β‐substituents are obtained in good yields and with the highest enantioselectivity reported to date. The presence of a secondary amine group was found to be crucial to achieve high stereocontrol.