✍ Scribed by Ferenc Faigl; Angelika Thurner; Ferenc Farkas; Melinda Battancs; László Poppe
No coin nor oath required. For personal study only.
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 (+)‐(2__R,__3__R,__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. Chirality, 2007. © 2006 Wiley‐Liss, Inc.
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