Enantioselective synthesis of axially chiral biaryls through rhodium-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes

被引:85
作者
Tanaka, K [1 ]
Nishida, G
Ogino, M
Hirano, M
Noguchi, K
机构
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Dept Appl Chem, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
关键词
D O I
10.1021/ol0511880
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a cationic rhodium(I)/H8-BINAP complex-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes with dialkyl acetylenedicarboxylates. This reaction was successfully applied to enantioselective synthesis of axially chiral biaryls utilizing internal alkynes bearing ortho-substituted phenyl and acetoxymethyl in each terminal position. The axial chirality is constructed at the formation of benzene rings with high enantioselectivity (up to 96% ee).
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页码:3119 / 3121
页数:3
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