Cationic iridium-catalyzed enantioselective activation of secondary sp3 C-H bond adjacent to nitrogen atom

被引：80
|
作者：
Pan, Shiguang [1 ]
Matsuo, Yusuke [1 ]
Endo, Kohei [2 ]
Shibata, Takanori [1 ]
机构：
[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Sci, Kanazawa, Ishikawa 9201192, Japan
来源：
TETRAHEDRON | 2012年 / 68卷 / 44期
关键词：
C-H activation; Enantioselective; Iridium; Heterocycle; REVERSIBLE ALPHA-ELIMINATION; COUPLING REACTION; ARYLATION; FUNCTIONALIZATION; PALLADIUM; ALKYNYLATION; ARYL; BORYLATION; COMPLEXES; SOLVENT;
D O I：
10.1016/j.tet.2012.08.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cationic Ir(I)-tolBINAP complex catalyzed an enantioselective C-C bond formation, which was initiated by secondary sp(3) C-H bond cleavage adjacent to nitrogen atom. A wide variety of 2-(alkylamino) pyridines and alkenes were selectively transformed into the corresponding chiral amines with moderate to almost perfect enantiomeric excesses. Alkynes were also investigated as coupling partners. The effect of alkyl structure in substrates and directing groups were studied. This transformation represents the first example of a highly enantioselective C-H bond activation of a methylene group, not at allylic or benzylic position. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9009 / 9015
页数：7
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