TY - JOUR
T1 - Metal-mediated, completely diastereofacial conjugate addition of trialkylstannylmetal reagents to γ-alkoxy-α,β-unsaturated esters
AU - Krief, A.
AU - Provins, L.
AU - Dumont, W.
PY - 1999/7/12
Y1 - 1999/7/12
N2 - Complete control of the face of attack in the addition of stannylmetal reagents to γ-alkoxy-α,β-unsaturated esters can be achieved by using the appropriate counterion (see scheme). The stereochemistry of addition does not depend on the configuration of the C-C double bond, although the stereoselectivity is consistently better with the Z stereoisomer, for which 100% Si attack is obtained with Li as counterion and 100% Re attack with LiZnEt.
AB - Complete control of the face of attack in the addition of stannylmetal reagents to γ-alkoxy-α,β-unsaturated esters can be achieved by using the appropriate counterion (see scheme). The stereochemistry of addition does not depend on the configuration of the C-C double bond, although the stereoselectivity is consistently better with the Z stereoisomer, for which 100% Si attack is obtained with Li as counterion and 100% Re attack with LiZnEt.
UR - http://www.scopus.com/inward/record.url?scp=0033549490&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1521-3773(19990712)38:13/14<1946::AID-ANIE1946>3.0.CO;2-9
DO - 10.1002/(SICI)1521-3773(19990712)38:13/14<1946::AID-ANIE1946>3.0.CO;2-9
M3 - Article
AN - SCOPUS:0033549490
SN - 1433-7851
VL - 38
SP - 1946
EP - 1948
JO - Angewandte Chemie. International edition
JF - Angewandte Chemie. International edition
IS - 13-14
ER -