Enantioselective synthesis of a hindered furyl substituted allyl alcohol intermediate: a case study in asymmetric synthesis

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Abstract

In the course of the synthesis of the DEFG ring system of cneorin C 1, we were faced with the task of preparing the furyl substituted allyl alcohol 5 enantioselectively. Several different methods starting from enantioselective zinc-mediated alkylations were attempted, but none of them proved entirely satisfactory. The solution turned out to be enzymatic kinetic resolution through a highly enantioselective (E > 300) acylation in the presence of Candida antarctica lipase A.

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Original languageEnglish
Pages (from-to)1637-1643
JournalTETRAHEDRON-ASYMMETRY
Issue number15
Publication statusPublished - 2004
MoE publication typeA1 Journal article-refereed

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