TY - JOUR
T1 - The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst
AU - Chen, Dianjun
AU - Guo, Li
AU - Kotti, S. R.S.Saibabu
AU - Li, Guigen
N1 - Funding Information:
We gratefully acknowledge the National Institutes of Health (CA 99995-1) and the Robert A. Welch Foundation (D-1361) for the generous support of this work. We also thank Cody Timmons for his assistance.
PY - 2005/5/23
Y1 - 2005/5/23
N2 - The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.
AB - The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.
UR - http://www.scopus.com/inward/record.url?scp=19344369706&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2005.03.038
DO - 10.1016/j.tetasy.2005.03.038
M3 - Article
AN - SCOPUS:19344369706
VL - 16
SP - 1757
EP - 1762
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 10
ER -