Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols

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• 作者：Lá ; szló ; Csaba Bencze^a ; Csaba Paizs^a ; Monica Ioana Toş ; a^a ; Florin Dan Irimie ; ^a ; ^{irimie@chem.ubbcluj.ro"" rel=""nofollow}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2011
• 出版时间：30 March 2011
• 年：2011
• 卷：22
• 期：6
• 页码：675-683
• 全文大小：479 K

文摘

Possible routes for the enzymatic transformation of various substituted 1-(5-phenylfuran-2-yl)ethane-1,2-diols and their mono- and diacetylated counterparts were studied. Combining the regioselectivity of LPS mediated acylation of the starting racemic diols, the stereoselectivity of LAK shown in the enantiomer selective transformation of the previously formed racemic primary acetates and the LPS mediated mild hydrolysis–alcoholysis of the resolution products, an efficient preparative scale procedure for the synthesis of various highly enantiomerically enriched (R)- and (S)-phenylfuran-2-yl-ethane-1,2-diols has been developed.