Resolution of 2,2-disubstituted epoxides via biocatalytic azidolysis.
A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl-disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio- and enantioselective 1-azido-2-arylpropan-2-ols in excellent yields. Furthermore, these intermediates were used for the preparation of enantiomerically enriched amino alcohols and aziridines containing a tertiary center.
Molinaro
Carmela
C
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Autoroute Transcanadienne, Kirkland, Quebec, Canada H9H 3L1. carmela_molinaro@merck.com
Guilbault
Audrey-Anne
AA
Kosjek
Birgit
B
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006867:Hydrolases / Q000378:metabolism*; D015394:Molecular Structure; D019810:Sodium Azide / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D001388:Aziridines; D004852:Epoxy Compounds; D019810:Sodium Azide; D006867:Hydrolases; C430848:halohydrin dehalogenase