Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[ b]furan derivative

Graphic 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...

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Bibliographic Details
Published in:Tetrahedron letters 2004-02, Vol.45 (8), p.1667-1670
Main Authors: Nemoto, Hisao, Tsutsumi, Hiroe, Yuzawa, Satomi, Peng, Xian, Zhong, Weihui, Xie, Jun, Miyoshi, Norikazu, Suzuki, Ichiro, Shibuya, Masayuki
Format: Article
Language:English
Subjects:
Acetal
Alkenyl ether
Chiral resolution
Thin layer chromatography
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Summary:Graphic 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 1H and 13C NMR of methyne group of the benzhydryl moiety.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.12.104