Enantioselective synthesis of C2-symmetric spirobipyridine ligands through cationic Rh(I)/modified-BINAP-catalyzed double [2+2+2] cycloaddition

被引:87
作者
Wada, Azusa [1 ]
Noguchi, Keiichi
Hirano, Masao
Tanaka, Ken
机构
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
关键词
D O I
10.1021/ol070129e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioenriched C-2-symmetric spirobipyridine ligands were efficiently synthesized through a cationic rhodium(I)/(R)-Segphos or (R)-H-8-BINAP complex-catalyzed enantioselective intramolecular double [2 + 2 + 2] cycloaddition of bis-diynenitriles.
引用
收藏
页码:1295 / 1298
页数:4
相关论文
共 70 条
[31]  
Saito T, 2001, ADV SYNTH CATAL, V343, P264, DOI 10.1002/1615-4169(20010330)343:3<264::AID-ADSC264>3.3.CO
[32]  
2-K
[33]  
Shinohara T, 2003, HETEROCYCLES, V59, P587
[34]   Selective syntheses of metalated pyridines from two different unsymmetrical acetylenes, a nitrile, and a titanium(II) alkoxide [J].
Suzuki, D ;
Tanaka, R ;
Urabe, H ;
Sato, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3518-3519
[35]   Formation of linear tetramers of diarylalkynes by the Zr/Cr system [J].
Takahashi, T ;
Liu, YH ;
Iesato, A ;
Chaki, S ;
Nakajima, K ;
Kanno, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11928-11929
[36]   Catalytic asymmetric synthesis of 1,1′-spirobi[indan-3,3′-dione] via a double intramolecular C-H insertion process [J].
Takahashi, T ;
Tsutsui, H ;
Tamura, M ;
Kitagaki, S ;
Nakajima, M ;
Hashimoto, S .
CHEMICAL COMMUNICATIONS, 2001, (17) :1604-1605
[37]   Selective formation of substituted pyridines from two different alkynes and a nitrile: Novel coupling reaction of azazirconacyclopentadienes with alkynes [J].
Takahashi, T ;
Tsai, FY ;
Kotora, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4994-4995
[38]  
Takizawa S, 2003, HETEROCYCLES, V60, P2551
[39]   Enantioselective synthesis of axially chiral anilides through rhodium-catalyzed [2+2+2] cycloaddition of 1,6-diynes with trimethylsilylynamides [J].
Tanaka, K ;
Takeishi, K ;
Noguchi, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4586-4587
[40]   Rhodium-catalyzed [2+2+2]cycloaddition of 1,6-diynes with isothiocyanates and carbon disulfide [J].
Tanaka, K ;
Wada, A ;
Noguchi, K .
ORGANIC LETTERS, 2006, 8 (05) :907-909