4.8 Article

Utilization of CO2 as a Cl Building Block in a Tandem Asymmetric A3 Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones

Journal

ACS CATALYSIS
Volume 7, Issue 12, Pages 8588-8593

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03370

Keywords

CO2 transformation; asymmetric tandem reaction; carboxylative cyclization; A(3) coupling; 2-oxazolidinone

Funding

  1. 973 Program [2015CB856600]
  2. NSFC [21502053, 21573073, 21472049, 21725203]

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We report a tandem asymmetric aldehyde-alkyne-amine (A(3)) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tandem reaction using CO2 as a Cl synthon. Notably, the copper species and ligand from the upstream A(3) reaction are internally reused to facilitate the downstream silver-catalyzed carboxylative cyclization.

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