Asymmetric Conjugate Addition of Benzofuran‐2‐ones to Alkyl 2‐Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters |
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| Authors: | Chen Yang En‐Ge Zhang Prof Xin Li Prof Jin‐Pei Cheng |
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| Institution: | State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China |
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| Abstract: | 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. |
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| Keywords: | amino acids asymmetric catalysis enantioselectivity free-energy relationships hydrogen bonds |
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