TY - JOUR
T1 - A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes
AU - Ito, Yoshio
AU - Terashima, Shiro
PY - 1987/1/1
Y1 - 1987/1/1
N2 - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.
AB - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.
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U2 - 10.1016/S0040-4039(00)96931-4
DO - 10.1016/S0040-4039(00)96931-4
M3 - Article
AN - SCOPUS:0001439535
VL - 28
SP - 6629
EP - 6632
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 52
ER -