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Enantiomer resolution by crystallization with chiral hosts: application to monoterpenes, verbenone and apoverbenone

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
7
Identifiers
DOI: 10.1016/0957-4166(95)00181-n

Abstract

Abstract Chiral hosts, (2 R,3 R)-(−)-2,3- O-isopropylidene-1,1,4,4-tetrakis(2-methylphenyl)-1,2,3,4-butanetetrol ( 1) and (2 R,3 R)-(−)-2,3- O-isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol ( 5), enantioselectively form crystalline 1:1 inclusion complexes with (1 S,5 S)-(−)-verbenone ( 2) and (1 R,5 R)-(+)-apoverbenone ( 6), respectively, and by applying this chiral discrimination in crystallization, enantiopure verbenone and apoverbenone are obtained.

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