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trans ‐2‐ tert ‐Butylcyclohexanol, a Simple Selectively Optimized Cyclohexanol Auxiliary
Author(s) -
Esser Peter,
Buschmann Helmut,
MeyerStork Markus,
Scharf HansDieter
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199211901
Subject(s) - cyclohexanol , saponification , simple (philosophy) , selectivity , chemistry , enantiomer , organic chemistry , catalysis , philosophy , epistemology
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.