Dinuclear zinc-catalyzed asymmetric [3 + 2] cyclization reaction for direct assembly of chiral α-amino-γ-butyrolactones bearing three stereocenters?

Organic Chemistry Frontiers Pub Date: 2021-11-06 DOI: 10.1039/D1QO01338F

Abstract

An efficient enantioselective [3 + 2] annulation of α-hydroxy-1-indanones and alkylidene azlactones has been developed with chiral dinuclear zinc catalysts via a Br?nsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral α-amino-γ-butyrolactones bearing three stereocenters in good yields with excellent diastereo- and enatiostereoselectivities (up to 88% yield, 20?:?1 dr, 99% ee). This transformation features broad functional group tolerance, gram-scale synthesis, and further prolongation with α-hydroxyacetophenone or 3-hydroxychroman-4-one.

Graphical abstract: Dinuclear zinc-catalyzed asymmetric [3 + 2] cyclization reaction for direct assembly of chiral α-amino-γ-butyrolactones bearing three stereocenters
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