TY - JOUR
T1 - Asymmetric synthesis of β-monosubstituted and β,β-disubstituted N- (p-toluenesulfinyl)-α-(aminoalkyl)acrylates via anionic additions of (α- carbalkoxyvinyl)cuprates to thiooxime S-oxides
AU - Wei, Han Xun
AU - Hook, Jason D.
AU - Fitzgerald, Keith A.
AU - Li, Guigen
N1 - Funding Information:
We gratefully acknowledge financial support from the Robert A. Welch Foundation (grant D-1361) and the Research Enhancement Fund of Texas Tech University for supporting this work. We also would like to thank Sun Hee Kim, Margaret Neighbors and Randy M. Tercero for their assistance.
PY - 1999/2/26
Y1 - 1999/2/26
N2 - A series of new Bayils-Hillman adducts, β-monosubstituted and β,β- disubstituted N-(p-toluenesulfinyl)-α-(aminoalkyl)acrylates has been synthesized via asymmetric nucleophilic additions of (α- carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines. Modest to good yields (52.0-72.0%) and excellent diastereoselectivity (>90% de) have been obtained. The Z/E selectivity was found to be effected by solvents or cosolvents.
AB - A series of new Bayils-Hillman adducts, β-monosubstituted and β,β- disubstituted N-(p-toluenesulfinyl)-α-(aminoalkyl)acrylates has been synthesized via asymmetric nucleophilic additions of (α- carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines. Modest to good yields (52.0-72.0%) and excellent diastereoselectivity (>90% de) have been obtained. The Z/E selectivity was found to be effected by solvents or cosolvents.
UR - http://www.scopus.com/inward/record.url?scp=0033605022&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(99)00036-1
DO - 10.1016/S0957-4166(99)00036-1
M3 - Article
AN - SCOPUS:0033605022
VL - 10
SP - 661
EP - 665
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 4
ER -