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Chiral Bis(imidazolinyl)phenyl NCN Pincer Rhodium(III) Catalysts for Enantioselective Allylation of Aldehydes and Carbonyl–Ene Reaction of Trifluoropyruvates

Author:
Wang, Tao, Hao, Xin-Qi, Huang, Juan-Juan, Niu, Jun-Long, Gong, Jun-Fang, Song, Mao-Ping
Source:
Journal of organic chemistry 2013 v.78 no.17 pp. 8712-8721
ISSN:
1520-6904
Subject:
alcohols, aldehydes, allylation, catalysts, chemical structure, enantioselectivity, esters, ligands, organic chemistry, rhodium, silver
Abstract:
Chiral NCN pincer rhodium(III) complexes with bis(imidazolinyl)phenyl ligands were found to be effective catalysts for the allylation of a variety of electronically and structurally diverse aldehydes with allyltributyltin, giving the corresponding optically active homoallylic alcohols in high yields with enantioselectivities of up to 97% ee. These complexes were also applied in the carbonyl–ene reaction of ethyl or methyl trifluoropyruvate with various 2-arylpropenes. With the aid of silver trifluoromethanesulfonate, the pincer rhodium(III) catalysts could catalyze the reaction to provide the corresponding chiral α-hydroxy-α-trifluoromethyl esters in good yields with high stereoselectivities (up to 95% ee).
Agid:
5500368