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Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis

2013; American Chemical Society; Volume: 135; Issue: 29 Linguagem: Inglês

10.1021/ja4052075

1943-2984

Wenbo Liu, Corey M. Reeves, Scott C. Virgil, Brian M. Stoltz,

Synthetic Organic Chemistry Methods

Highly congested vicinal stereocenters comprised of tertiary and all-carbon quaternary centers were generated via Ir-catalyzed asymmetric allylic alkylation of β-ketoesters. These catalytic reactions proceed in excellent yields with a broad scope on either reaction partner and with outstanding regio-, diastereo-, and enantiocontrol. Implementation of a subsequent Pd-catalyzed alkylation affords dialkylated products with pinpoint stereochemical control of both chiral centers.