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Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution
Author(s) -
Bertozzi Fabio,
Crotti Paolo,
Macchia Franco,
Pineschi Mauro,
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<930::aid-anie930>3.0.co;2-7
Subject(s) - enantioselective synthesis , kinetic resolution , phosphoramidite , chemistry , enantiomer , ligand (biochemistry) , catalysis , reactivity (psychology) , stereochemistry , combinatorial chemistry , organic chemistry , receptor , medicine , dna , biochemistry , alternative medicine , pathology , oligonucleotide
Chiral recognition leads to enantio‐ and regiodivergent reactivity: An unusual regiodivergent catalytic kinetic resolution has been accomplished for the first time in an organometallic reaction in which a C−C bond is formed. Chiral copper complexes of the non‐racemic phosphoramidite ligand L* discriminate the enantiomers of semirigid vinyloxiranes (having a blocked s‐ cis or s‐ trans conformation) to give separable regioisomeric products with very high stereocontrol in a two‐step process (see scheme).