Enzymatic resolution of homoallyllic alcohols using various Rhizopus species.
The asymmetric resolution of various 1-aryl-3-buten-1-ols via microbial hydrolysis of the corresponding acetates has been investigated using different Rhizopus species. The chosen species, R. arrhizus (wild type), efficiently hydrolyzed 1-phenyl- and 1-para-substituted phenyl-3-buten-1-ol acetates, producing the enantiomerically pure (R)-alcohols with 53-65% yields. Although the antipode acetates were obtained with 9-52% enantiomeric excess, the (S)-alcohols were amenable in >99% enantiomeric excess via a R. arrhizus mediated asymmetric reduction of the corresponding ketones.
Salvi
Neeta A
NA
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 40085, India.
Badheka
Lalit P
LP
Chattopadhyay
Subrata
S
D000085:Acetates / Q000378:metabolism*; D000438:Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D000498:Allyl Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D006868:Hydrolysis; D012233:Rhizopus / Q000145:classification / Q000201:enzymology* / Q000378:metabolism; D013045:Species Specificity; D013237:Stereoisomerism; D013379:Substrate Specificity
D000085:Acetates; D000438:Alcohols; D000498:Allyl Compounds