Enantioselective sp3 C–H alkylation of γ-butyrolactam by a chiral Ir(i) catalyst for the synthesis of 4-substituted γ-amino acids?

Chemical Communications Pub Date: 2015-09-21 DOI: 10.1039/C5CC07102J

Abstract

Ir-catalyzed sp3 C–H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

Graphical abstract: Enantioselective sp3 C–H alkylation of γ-butyrolactam by a chiral Ir(i) catalyst for the synthesis of 4-substituted γ-amino acids
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