Candida antarctica lipase B (CAL-B)-catalyzed N-acylation with 2,2,2-trifluoroethyl butanoate in solvent mixtures of tert-butyl methyl ether and tert-amyl alcohol was used to prepare all the enantiomers of cis- and trans-2-aminocyclopentane- and -cyclohexanecarboxamides. An unexpected change in enantiopreference, accompanied by low enantioselectivity, was observed when Pseudomonas cepacia lipase (cis-cyclohexane substrate) or C. antarctica lipase A (cis-cyclopentane and -cyclohexane substrates) replaced CAL-B.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry