408305-22-6Relevant articles and documents
Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides
Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V. A.,Faber, Kurt
, p. 4537 - 4542 (2001)
Biocatalytic hydrolysis of 2,3-disubstituted rac-cis- and rac-trans-haloalkyl epoxides 1a-8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b-8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c-6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted in the formation of single stereoisomeric products in 100% des and up to 92% ees from the racemates.