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Synthesis of Enantiomerically Pure Cyclohex‐2‐en‐1‐ols: Development of Novel Multicomponent Reactions
Author(s) -
Strübing Dirk,
Kirschner Anett,
Neumann Helfried,
Hübner Sandra,
Klaus Stefan,
Bornscheuer Uwe T.,
Beller Matthias
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401258
Subject(s) - kinetic resolution , toluene , enantiomer , chemistry , catalysis , organic chemistry , alkoxy group , stereoselectivity , combinatorial chemistry , enantioselective synthesis , alkyl
Multicomponent reactions of aldehydes, dienophiles, and alcohols or carboxylic acid anhydrides have been developed for the first time. In situ generation of 1‐acyloxy‐ and 1‐alkoxy‐1,3‐butadiene derivatives in toluene in the presence of electron‐deficient dienophiles provides selective and efficient access to functionalized cyclohex‐2‐ene‐1‐ols in good yields. Subsequent enzyme‐catalyzed kinetic resolution gave the corresponding enantiomers with high enantioselectivity.