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

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• 作者：Ansoo Lee ; Hyunwoo Kim
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3520-3527
• 全文大小：466K
• 年卷期：0
• ISSN：1520-6904

文摘

A complementary solution for Rh-catalyzed enantioselective 1,2- and 1,4-arylation with two structurally related chiral ligands is reported. A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from 1-aminoindane was efficient for the 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 was found to selectively provide γ,γ-diaryl N-tosyl enamines with high yields and stereoselectivities.