H. Nemoto, H. Tsutsumi, Satomi Yuzawa
Feb 16, 2004
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
The reaction of 3a-benzhydryl-3,3a,4,5-tetrahydro-2 H -cyclopenta[ b ]furan and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichloromethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[ b ]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large Δ R f value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of 1 H and 13 C NMR of methyne group of the benzhydryl moiety.