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Copper‐catalyzed divergent kinetic resolution of racemic allylic substrates
Author(s) -
Pineschi Mauro,
Bussolo Valeria DI,
Crotti Paolo
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20980
Subject(s) - stereocenter , kinetic resolution , chemistry , allylic rearrangement , tsuji–trost reaction , reagent , chirality (physics) , stereoselectivity , catalysis , combinatorial chemistry , substrate (aquarium) , copper , stereochemistry , enantioselective synthesis , organic chemistry , chiral symmetry breaking , physics , oceanography , quantum mechanics , quark , geology , nambu–jona lasinio model
When a racemic mixture is fully consumed the products may still be enantiomerically enriched. In particular, the regiodivergent kinetic resolution is a process in which a single chiral catalyst or reagent reacts with a racemic substrate to form regioisomers possessing an opposite configuration on the newly‐formed stereogenic centers. This review reports the major advances in the field of the copper‐catalyzed regiodivergent and stereodivergent kinetic resolution of allylic substrates with organometallic reagents . The chiral recognition matching phenomena found with particular allylic substrates with the absolute configuration of the chiral catalyst allows in some cases an excellent control of the regio‐ and stereoselectivity, sheding some light on the so‐called “black‐box” mechanism of a copper‐catalyzed asymmetric allylic alkylation . Chirality, 2011. © 2011 Wiley‐Liss, Inc.