【Jinpei Cheng Group】Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters-元素有机化学国家重点实验室

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【Jinpei Cheng Group】Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters

Source：SKLEOC Date：2016/10/11

The free-energy relationships between the stereoselectivities and the properties of tertiary amine thiourea catalysts were investigated by combining steric and electronic parameters for the first time. Prof. Xin Li and Prof. Jinpei Cheng have found that thioureas with small, strongly electron-withdrawing N substituents were shown to be optimal catalysts for the Michael addition of 3-substituted benzofuranones and alkyl 2-phthalimidoacrylates. As a result, the methyl- and 3,5-bis(trifluoromethyl)benzyl-substituted tertiary amine thioureas identified during the free-energy analysis were successfully applied for the synthesis of α-amino acid derivatives with a benzofuran-2-one in the γ-position and 1,3-nonajacent stereogenic centers in high yields and stereoselectivities.

Link: http://onlinelibrary.wiley.com/doi/10.1002/anie.201601028/full .

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