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Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands

Ansoo Lee and Hyunwoo Kim*

*Department of Chemistry, KAIST, Daejeon 34141, Korea, Email: hwkimkaist.edu

A. Lee, H. Kim, J. Am. Chem. Soc., 2015, 137, 11250-11253.

DOI: 10.1021/jacs.5b07034


Abstract

A chiral bicyclic bridgehead phosphoramidite (briphos) is a highly efficient and selective ligand for Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated N,N-dimethyl-sulfamoyl imino esters at ambient temperature providing chiral (Z)-γ,γ-diaryl-α,β-dehydroamino esters with excellent yield and enantioselectivity, that can be further converted to unnatural amino acids, hydroxy ketones, and keto acids.

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Chiral Bicyclic Bridgehead Phosphoramidite (Briphos) Ligands for Asymmetric Rhodium-Catalyzed 1,2- and 1,4-Addition

A. Lee, H. Kim, J. Org. Chem., 2016, 81, 3520-3527.


Key Words

arylation


ID: J48-Y2015