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

Ansoo Lee and Hyunwoo Kim*

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

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

DOI: 10.1021/acs.joc.6b00033 (free Supporting Information)



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Abstract

A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from 1-aminoindane was efficient for the Rh-catalyzed enantioselective 1,2-arylation of N-sulfonyl imines, while that derived from 1,2,3,4-tetrahydro-1-naphthylamine was efficient for 1,4-arylation of α,β-unsaturated cyclic ketones. For α,β-unsaturated N-tosyl ketimines, the briphos derived from 1-aminoindane selectively provided γ,γ-diaryl N-tosyl enamines.

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

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


Key Words

1,2-arylation, 1,4-arylation


ID: J42-Y2016