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Asymmetric Conjugate Addition of Benzofuran‐2‐ones to Alkyl 2‐Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters
Author(s) -
Yang Chen,
Zhang EnGe,
Li Xin,
Cheng JinPei
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601028
Subject(s) - steric effects , stereocenter , chemistry , stereoselectivity , amine gas treating , conjugate , benzofuran , alkyl , tertiary amine , catalysis , thiourea , trifluoromethyl , electronic effect , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , mathematics
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.