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Remote asymmetric conjugate addition catalyzed by a bifunctional spiro-pyrrolidine-derived thiourea catalyst

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A novel spiro-pyrrolidine (SPD)-derived bifunctional thiourea catalyst has been developed, enabling the development of a stereoselective conjugate addition of furfurals to β,γ-unsaturated α-ketoesters. The reaction represents an example of asymmetric… Click to show full abstract

A novel spiro-pyrrolidine (SPD)-derived bifunctional thiourea catalyst has been developed, enabling the development of a stereoselective conjugate addition of furfurals to β,γ-unsaturated α-ketoesters. The reaction represents an example of asymmetric trienamine catalysis in the benzylic C–H functionalization of 5-benzylfurfurals, and the rigid spirocyclic framework of the catalyst is proven to be essential for a highly enantioselective transformation.

Keywords: catalyst; conjugate addition; thiourea catalyst; spiro pyrrolidine

Journal Title: Organic chemistry frontiers
Year Published: 2021

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