Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides

Chem Sci. 2021 Jul 7;12(33):11191-11196. doi: 10.1039/d1sc02439f. eCollection 2021 Aug 25.

ABSTRACT

Described here is the first organocatalytic asymmetric N-H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions. As a stable surrogate of diazocarbonyl compounds, sulfoxonium ylides reacted with a range of aryl amines to provide efficient access to α-aryl glycines with excellent enantiocontrol in the presence of a suitable chiral phosphoric acid catalyst. The high stability and weak basicity of sulfoxonium ylides not only enable this protocol to be user-friendly and practically useful, but also preclude catalyst decomposition, which is crucial to the excellent amenability to electron-poor amine nucleophiles. Detailed mechanistic studies indicated that the initial protonation is reversible and the C-N bond formation is rate-determining.

PMID:34522316 | PMC:PMC8386753 | DOI:10.1039/d1sc02439f

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