Catalytic Enantioselective Synthesis of Atropisomeric Indoles with an N-C Chiral Axis

被引:140
作者
Ototake, Nobutaka [1 ]
Morimoto, Yudai [1 ]
Mokuya, Ayano [1 ]
Fukaya, Haruhiko [2 ]
Shida, Yasuo [2 ]
Kitagawa, Osamu [1 ]
机构
[1] Shibaura Inst Technol, Dept Appl Chem, Koto Ku, Tokyo 1358548, Japan
[2] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan
关键词
atropisomerism; enantioselectivity; indoles; palladium; phosphane ligands; NON-BIARYL ATROPISOMERS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ANILIDES; BOND; CYCLOADDITION; DERIVATIVES; CYCLIZATION; ALLYLATION; RESOLUTION;
D O I
10.1002/chem.201000243
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A pivotal role: In the presence of (R)-(-)-5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4, 4′-bi-1,3-benzodioxole-PdCl2 [(R)-SEGPHOS-PdCl2], 5-endo-hydroaminocyclization of achiral ortho-alkynylanilines proceeds in an enantioselective manner to give optically active, axially chiral indoles (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6752 / 6755
页数:4
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