Publication | Closed Access
Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ‐Substituted Allenes and Electron‐Poor Olefins
38
Citations
54
References
2015
Year
Novel OrganocatalystsDerivativesEngineeringAlkene MetathesisCyclopentene DerivativesNew Chiral PhosphahelicenesDiversity-oriented SynthesisEnantioselective OrganocatalysisNatural SciencesOrganic Chemistryγ‐Substituted AllenesStereoselective SynthesisChemistryAsymmetric CatalysisAsymmetric OrganocatalysisEnantioselective SynthesisBiomolecular EngineeringElectron‐poor Olefins
Abstract The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene‐ or alkylidenemalononitriles and γ‐substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.
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