Lipase mediated enantiomer and diastereomer separation of 2,2′-[1,2- and 1,3-phenylenebis(oxy)]dicyclohexanols | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8723203

Reference Type

Journal Article

Title

Lipase mediated enantiomer and diastereomer separation of 2,2′-[1,2- and 1,3-phenylenebis(oxy)]dicyclohexanols

Author(s)

Toke, ER; Kolonits, P; Novák, L; Poppe, L

Year

2006

Is Peer Reviewed?

Journal

Tetrahedron: Asymmetry
ISSN: 0957-4166

Publisher

Elsevier

Location

OXFORD

Volume

Issue

Page Numbers

2377-2385

Language

English

DOI

10.1016/j.tetasy.2006.08.015

Web of Science Id

WOS:000241610100011

Abstract

Separation of diastereomeric and enantiomeric mixtures of 2,2′-[1,2- and 1,3-phenylenebis(oxy)]dicyclohexanols rac-3a and meso-3a, and rac-3b and meso-3b-resulting from the reactions of pyrocatechol 1a and resorcinol 1b with cyclohexene oxide 2-were performed using acetylation catalyzed by the highly stereoselective Candida antarctica lipase B (Novozym 435). The absolute configurations of the resulting diols (S,S,S,S)-3a,b, monoacetates (R,R,S,S)-4a,b and diacetates (R,R,R,R)-5a,b were assigned on the basis of the steric analogy to the acetylation of racemic trans-2-phenoxycyclohexanol rac-6 with the same enzyme resulting in the known acetate (-)-(R,R)-7. 2006 Elsevier Ltd. All rights reserved.

Series

TETRAHEDRON-ASYMMETRY