Enantioselective synthesis of helical molecules: Lipase-catalyzed resolution of bis(hydroxymethyl)[7]thiaheterohelicene
摘要：
Lipase ( Pseudomonas cepacia )-catalyzed transesterification of racemic 2, 13-bis(hydroxymethyl)dithieno[3,2-e:3′,2′-e′]benzo[1,2-b:4,3-b′]bis[1]benzothiophene by vinyl acetate in dichloromethane proceeded with a high degree of enantioselectivity to give ( P )-(+)-bis(hydroxymethyl)[7]thiaheterohelicene (45% yield, 98% ee), and the corresponding monoacetate (37% yield) and diacetate (13% yield). Reduction of the monoester by LiAlH 4 gave ( M )-()-bis(hydroxymethyl)[7]thiaheterohelicene with 80% ee and the diester gave the same enantiomer with 95% ee. The reaction of the racemic helicenediol with Candida antarctica afforded the antipode with 92% ee.
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DOI：
10.1016/0040-4039(95)00128-Y
被引量：
年份：
1995
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