TY - JOUR
T1 - Asymmetric synthesis of chiral β-iodo Baylis-Hillman esters using MgI2 as promoter via a one-pot three-component reaction
AU - Wei, Han Xun
AU - Chen, Dianjun
AU - Xu, Xin
AU - Li, Guigen
AU - Paré, Paul W.
N1 - Funding Information:
We gratefully acknowledge the Robert A. Welch Foundation (D-478 and D-1361) for the generous support of this research. Funding was also provided by the Texas Excellence Fund.
PY - 2003/4/18
Y1 - 2003/4/18
N2 - An asymmetric synthesis of β-iodo-α-(hydroxyalkyl)acrylates has been developed involving conjugate addition of I- to menthyl propiolates to give β-iodo allenolate intermediates which undergo 1,2-addition to form β-iodo Baylis-Hillman products. Modest diastereoselectivities (37-58% de) and excellent yields (80-87%) were obtained when (1R,2S,5R)-(-)-menthol was used as a chiral auxiliary. The two diastereoisomers of the product were separated by silica gel chromatography to give diastereomerically pure products.
AB - An asymmetric synthesis of β-iodo-α-(hydroxyalkyl)acrylates has been developed involving conjugate addition of I- to menthyl propiolates to give β-iodo allenolate intermediates which undergo 1,2-addition to form β-iodo Baylis-Hillman products. Modest diastereoselectivities (37-58% de) and excellent yields (80-87%) were obtained when (1R,2S,5R)-(-)-menthol was used as a chiral auxiliary. The two diastereoisomers of the product were separated by silica gel chromatography to give diastereomerically pure products.
UR - http://www.scopus.com/inward/record.url?scp=0037453404&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(03)00115-0
DO - 10.1016/S0957-4166(03)00115-0
M3 - Article
AN - SCOPUS:0037453404
SN - 0957-4166
VL - 14
SP - 971
EP - 974
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 8
ER -