Premium
Highly Enantioselective Copper–Phosphoramidite Catalyzed Kinetic Resolution of Chiral 2‐Cyclohexenones
Author(s) -
Naasz Robert,
Arnold Leggy A.,
Minnaard Adriaan J.,
Feringa Ben L.
Publication year - 2001
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 - 10.1002/1521-3773(20010302)40:5<927::aid-anie927>3.0.co;2-k
Subject(s) - phosphoramidite , kinetic resolution , enantioselective synthesis , cyclohexenone , catalysis , copper , resolution (logic) , chemistry , combinatorial chemistry , selectivity , organic chemistry , computer science , oligonucleotide , dna , biochemistry , artificial intelligence
A variety of substituted 2‐cyclohexenones , such as ( R )‐ 1 , is obtained enantiomerically pure by employing the chiral copper–phosphoramidite complex [Cu(OTf) 2 L*] as a highly efficient catalyst for their kinetic resolution (>99 % ee at 52 % conversion, selectivity S >200). These important building blocks can be obtained on a synthetically interesting scale, as was demonstrated by the successful multigram resolution of 5‐methyl‐2‐cyclohexenone. Tf=trifluoromethanesulfonyl.