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Enantioselective and Catalytic Method for α‐Crotylation of Aldehydes with a Kinetic Self‐Refinement of Stereochemistry
Author(s) -
Malkov Andrei V.,
Kabeshov Mikhail A.,
Barłog Maciej,
Kočovský Pavel
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802224
Subject(s) - enantioselective synthesis , stereoselectivity , yield (engineering) , catalysis , kinetic resolution , refinery , chemistry , kinetic energy , one step , organic chemistry , stereochemistry , combinatorial chemistry , thermodynamics , chemical engineering , physics , quantum mechanics , engineering
Kinetic refinery : A practical, highly stereoselective, two‐step catalytic protocol for the α‐allylation of aldehydes, starting from crotyltrichlorosilanes, has been developed (see scheme). In each reaction step, one of the stereoisomers reacted faster than the other, which resulted in a kinetic stereochemical ( E / Z ) self‐refinement of the system and led to the formation of virtually enantiomerically and geometrically pure linear homoallylic alcohols in high yield.No Abstract