Synthesis of Chiral Tetrasubstituted Alkenes by an Asymmetric Cascade Reaction Catalyzed Cooperatively by Cationic Rhodium(I) and Silver(I) Complexes

被引：52
作者：
Hojo, Daiki
Noguchi, Keiichi [2 ]
Tanaka, Ken [1 ]
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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 43期
关键词：
alkenes; asymmetric catalysis; cascade reactions; helical chirality; rhodium; INTERMOLECULAR 4+2 CARBOCYCLIZATION; CONTAINING CARBONYL YLIDES; PLATINUM(II)-CATALYZED REACTION; CYCLOADDITION REACTIONS; BENZANNULATION; TANDEM; ANNULATION; 4-ALKYNALS; ENYNALS; O-ALKYNYL(OXO)BENZENES;
D O I：
10.1002/anie.200904024
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Fantastic four: Tetrasubstituted alkenes have been prepared with high enantioselectivity by the title transformation. This reaction was successfully applied to the enantio- and diastereoselective synthesis of tetrasubstituted helical alkenes possessing both central and helical chirality (see scheme). © 2009 Wiley-VCH Verlag.
引用
收藏
页码：8129 / 8132
页数：4
相关论文
共 46 条
[1]  
[Anonymous], 2003, ANGEW CHEM
[2]   AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].
Asao, N ;
Aikawa, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459
[3]   Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].
Asao, N ;
Kasahara, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506
[4]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[5]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[6]   AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].
Asao, N ;
Sato, K ;
Menggenbateer ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685
[7]   AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo) benzene and benzyne [J].
Asao, Naoki ;
Sato, Kenichiro .
ORGANIC LETTERS, 2006, 8 (23) :5361-5363
[8]   Gold- and copper-catalyzed [4+2] benzannulations between enynal or enynone units and 2π-systems [J].
Asao, Naoki .
SYNLETT, 2006, (11) :1645-1656
[9]   Lewis acid-catalyzed [4+2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives [J].
Asao, Naoki ;
Aikawa, Haruo .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5249-5253
[10]   Discovery of chemical reactions through multidimensional screening [J].
Beeler, Aaron B. ;
Su, Shun ;
Singleton, Chris A. ;
Porco, John A., Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1413-1419
12345