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Highly Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc Reagents
Author(s) -
Feringa Ben L.,
Pineschi Mauro,
Arnold Leggy A.,
Imbos Rosalinde,
de Vries André H. M.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199726201
Subject(s) - conjugate , enantioselective synthesis , phosphoramidite , trifluoromethanesulfonate , reagent , aldol reaction , chemistry , catalysis , combinatorial chemistry , zinc , addition reaction , ligand (biochemistry) , copper , organic chemistry , medicinal chemistry , mathematics , dna , mathematical analysis , biochemistry , receptor , oligonucleotide
Complete stereocontrol with the added advantage of functional‐group tolerance in copper‐catalyzed 1,4‐additions of organozinc reagents to enones has been achieved for the first time with the chiral phosphoramidite L * as ligand in the copper complex [Eq. (a), Tf = trifluoromethanesulfonate]. The zinc enolate intermediate of the reaction can be trapped with aldehydes.