Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure-Stereoselectivity Relationships with Steric and Electronic Parameters

A highly predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of Michael reactions of 3‐substituted benzofuranones and alkyl 2‐phthalimidoacrylates is described. As predicted, new 3,5‐bis(trifluoromethyl)benzyl‐ and methyl...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-05, Vol.55 (22), p.6506-6510
Main Authors: Yang, Chen, Zhang, En-Ge, Li, Xin, Cheng, Jin-Pei
Format: Article
Language:English
Subjects:
Amino acids
asymmetric catalysis
Asymmetry
Benzofuran
Catalysts
Chemical synthesis
Correlation
Derivatives
enantioselectivity
free-energy relationships
hydrogen bonds
Mathematical models
Stereoselectivity
Thiourea
Thioureas
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Summary:A highly predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of Michael reactions of 3‐substituted benzofuranones and alkyl 2‐phthalimidoacrylates is described. As predicted, new 3,5‐bis(trifluoromethyl)benzyl‐ and methyl‐substituted tertiary amine thioureas turned out to be highly suitable catalysts for this reaction and enabled the synthesis of enantioenriched α‐amino acid derivatives with 1,3‐nonadjacent stereogenic centers. A predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of the title reaction is described. As predicted, 3,5‐bis(trifluoromethyl)benzyl‐ and methyl‐substituted tertiary amine thioureas turned out to be highly suitable catalysts.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201601028