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Variable C 2 ‐Symmetric Analogues of N ‐Hydroxyphthalimide as Enantioselective Catalysts for Aerobic Oxidation: Kinetic Resolution of Oxazolidines
Author(s) -
Nechab Malek,
Kumar Dhondi Naveen,
Philouze Christian,
Einhorn Cathy,
Einhorn Jacques
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603780
Subject(s) - oxazolidine , kinetic resolution , enantioselective synthesis , catalysis , chemistry , kinetic energy , stereoselectivity , ring (chemistry) , resolution (logic) , combinatorial chemistry , organic chemistry , medicinal chemistry , polymer chemistry , physics , computer science , quantum mechanics , artificial intelligence
Fast and selective : The aerobic oxidative ring opening of oxazolidine 1 in the presence of a catalytic amount of the chiral N ‐hydroxyphthalimide analogue 2 was accompanied by efficient kinetic resolution of the oxazolidine. Thus, 50.5 % conversion was attained within 2 h, and the remaining 1 had an ee value of 89 %. The corresponding stereoselectivity factor, s = k rel(fast/slow) , is very high at around 40.