TRANS-2-TERT-BUTYLCYCLOHEXANOL, A SIMPLE SELECTIVELY OPTIMIZED CYCLOHEXANOL AUXILIARY

An economical auxiliary comparable to 8-phenylmenthol, trans-2-tert-butylcyclohexanol (1) was derived as a "structurally minimized" cyclohexanol with an optimized induction potential by application of the isoinversion principle and the structure-selectivity relationship of the cyclohexanol...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 31; no. 9; pp. 1190 - 1192
Main Authors ESSER, P, BUSCHMANN, H, MEYERSTORK, M, SCHARF, HD
Format Journal Article
LanguageEnglish
Published DEERFIELD BEACH Wiley 01.09.1992
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ROUTE
SOLVENTS
ASYMMETRIC INDUCTION
ENZYMES
RESOLUTION
CHIRAL AUXILIARIES
ENZYMATIC-HYDROLYSIS
ENE REACTIONS
PIG-LIVER ESTERASE
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Summary:An economical auxiliary comparable to 8-phenylmenthol, trans-2-tert-butylcyclohexanol (1) was derived as a "structurally minimized" cyclohexanol with an optimized induction potential by application of the isoinversion principle and the structure-selectivity relationship of the cyclohexanol auxiliaries. A simple preparation of both enantiomers of 1 is possible on a large scale by the enzymatic saponification of a technical-grade product.
ISSN:0570-0833
DOI:10.1002/anie.199211901