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Enzyme‐Triggered Enantioconvergent Transformation of Haloalkyl Epoxides
Author(s) -
Mayer Sandra F.,
Steinreiber Andreas,
Orru Romano V. A.,
Faber Kurt
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.0.co;2-e
Subject(s) - chemistry , vicinal , yield (engineering) , epoxide , stereochemistry , enzyme , epoxide hydrolase , hydrolysis , stereoselectivity , transformation (genetics) , organic chemistry , ring (chemistry) , catalysis , biochemistry , materials science , metallurgy , microsome , gene
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% de s and up to 92% ee s from the racemates.