Journal
ORGANIC LETTERS
Volume 25, Issue 47, Pages 8445-8450Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c03341
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This study presents a new method for the asymmetric synthesis of spiroxindole cyclopentanes containing five stereocenters. The strategy demonstrated a broad substrate scope and high selectivity.
Despite the widespread presence of the chiral cyclopentane motif, the asymmetric synthesis of cyclopentanes containing five stereocenters remains a formidable challenge. Here, we present an N-heterocyclic carbene (NHC)-catalyzed cascade reaction of enal and oxindole-dienone, which allows access to spiroxindole cyclopentanes featuring a complete set of chiral centers on the five-membered carbocycle. This strategy, characterized by the formation of multiple bonds and chiral centers, demonstrates a broad substrate scope, exclusive diastereoselectivity, and up to 99:1 er.
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