79520-50-6Relevant academic research and scientific papers
An enzyme-triggered enantio-convergent cascade-reaction
Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V.A.,Faber, Kurt
, p. 41 - 43 (2001)
The biocatalytic hydrolysis of the (±)-2,3-disubstituted cis-chloroalkyl epoxides 1a and 2a using resting cells of Rhodococcus sp. did not give the corresponding chloroalkyl vic-diols 1b, and 2b, respectively, but furnished the rearranged products (2R,3R)-1c and (2R,3R)-2c in high e.e. as the sole products via an enzyme-triggered enantio-convergent cascade-reaction.
Enzyme-triggered enantioconvergent transformation of haloalkyl epoxides
Mayer, Sandra F.,Steinreiber, Andreas,Orru, Romano V. A.,Faber, Kurt
, p. 4537 - 4542 (2007/10/03)
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.
