Synthesis and enantioselective rearrangement of (Z)-4-triphenylmethoxy-2,3-epoxybutan-1-ol enantiomers.
Efficient enzyme catalyzed kinetic resolutions of a synthetically useful chiral building block, (Z)-4-triphenylmethoxy-2,3-epoxybutan-1-ol, are reported. The highest selectivities were achieved by Lipozyme TL IM and Amano Lipase PS enzymes in the presence of vinyl acetate. Enantiomeric enrichment of the optically active acetate isomer was accomplished by selective crystallization of the racemic part of the enantiomeric mixture. Enzyme catalyzed hydrolysis of the acetate also provided an optically pure epoxybutanol derivative. O-Benzylation of (+)-(Z)-1-hydroxy-4-triphenylmethoxy-2,3-epoxybutane followed by super base promoted diastereo- and enantio-selective rearrangement resulted in (+)-(2R,3R,1'R)-3-[1-hydroxy-2-(triphenylmethoxy)ethyl]-2-phenyloxetane in >98% ee and de. Configurations of the new optically active products were determined by chemical correlation.
Faigl
Ferenc
F
Department of Organic Chemical Technology, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 8., Hungary. ffaigl@mail.bme.hu
Thurner
Angelika
A
Farkas
Ferenc
F
Battancs
Melinda
M
Poppe
László
L
D000440:Butanols / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014320:Triphenylmethyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000440:Butanols; D004852:Epoxy Compounds; D014320:Triphenylmethyl Compounds