TY - JOUR
T1 - Direct catalytic asymmetric intramolecular conjugate addition of thioamide to α,β-unsaturated esters
AU - Suzuki, Yuta
AU - Yazaki, Ryo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2011/10/17
Y1 - 2011/10/17
N2 - Proton transfer allows efficient access to optically active five- and six-membered ring systems bearing ester and thioamide functionalities in an anti fashion; these ring systems are amenable to differential functional group manipulation. Direct catalytic, asymmetric, intramolecular conjugate addition of thioamide to α,β-unsaturated esters is described. In situ generated Cu thioamide enolate, by catalytic deprotonation, underwent the conjugate addition/protonation, to achieve the complete transformation (see scheme).
AB - Proton transfer allows efficient access to optically active five- and six-membered ring systems bearing ester and thioamide functionalities in an anti fashion; these ring systems are amenable to differential functional group manipulation. Direct catalytic, asymmetric, intramolecular conjugate addition of thioamide to α,β-unsaturated esters is described. In situ generated Cu thioamide enolate, by catalytic deprotonation, underwent the conjugate addition/protonation, to achieve the complete transformation (see scheme).
KW - atom economy
KW - conjugate addition
KW - cooperative catalysis
KW - proton transfer
KW - thioamides
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U2 - 10.1002/chem.201102332
DO - 10.1002/chem.201102332
M3 - Article
C2 - 21932244
AN - SCOPUS:80054026902
VL - 17
SP - 11998
EP - 12001
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 43
ER -