Variable  C  2 ‐Symmetric Analogues of  N ‐Hydroxyphthalimide as Enantioselective Catalysts for Aerobic Oxidation: Kinetic Resolution of Oxazolidines | Zendy

Nechab Malek | Zendy; Kumar Dhondi Naveen | Zendy; Philouze Christian | Zendy; Einhorn Cathy | Zendy; Einhorn Jacques | Zendy

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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.

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