Article

Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes.

Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695 019, India.
Organic Letters (impact factor: 5.86). 06/2009; 11(12):2507-10. DOI:10.1021/ol900571x pp.2507-10
Source: PubMed

ABSTRACT Homoenolates generated from enals by nucleophilic heterocyclic carbene (NHC) catalysis undergo annulation with chalcones in methanol to afford methyl beta-hydroxycyclopentanecarboxylates, stereoselectively. Construction of four contiguous stereocenters in a stereoselective manner is noteworthy.

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Keywords

chalcones
 
contiguous stereocenters
 
methyl beta-hydroxycyclopentanecarboxylates
 
nucleophilic heterocyclic carbene
 
stereoselective manner