Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols

被引:227
作者
Nemoto, Tetsuhiro [1 ]
Ishige, Yuta [1 ]
Yoshida, Mariko [1 ]
Kohno, Yuta [1 ]
Kanematsu, Mutsumi [1 ]
Hamada, Yasumasa [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC-SYNTHESIS; QUATERNARY STEREOCENTERS; CYCLIZATION; ALLYLATION; METAL; DEAROMATIZATION; NUCLEOPHILES; COMPLEXES; KETONES;
D O I
10.1021/ol102190s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first successful Pd-catalyzed intramolecular ipso-Friedel Crafts allylic alkylation of phenols, which provided a new access to spiro[4.5]cyclohexadienones, is described. The present method could be applied to catalytic enantioselective construction of an all-carbon quaternary spirocenter.
引用
收藏
页码:5020 / 5023
页数:4
相关论文
共 48 条
[1]  
Appel TR, 2003, EUR J ORG CHEM, V2003, P47
[2]   NEIGHBORING CARBON AND HYDROGEN .46. SPIRO-(4,5)-DECA-1,4-DIENE-3-ONE FROM AR1THETA-5 PARTICIPATION [J].
BAIRD, R ;
WINSTEIN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :788-&
[3]   Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation [J].
Bandini, M ;
Melloni, A ;
Piccinelli, F ;
Sinisi, R ;
Tommasi, S ;
Umani-Ronchi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1424-1425
[4]   Ligand-Free Silver(I)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Arenes with Allylic Alcohols [J].
Bandini, Marco ;
Eichholzer, Astrid ;
Kotrusz, Peter ;
Tragni, Michele ;
Troisi, Stefano ;
Umani-Ronchi, Achille .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) :319-324
[5]   Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].
Chiba, Shunsuke ;
Zhang, Line ;
Lee, Jian-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+
[6]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[7]  
2-V
[8]   Atom transfer cyclization catalyzed by InCl3 via halogen activation [J].
Cook, GR ;
Hayashi, R .
ORGANIC LETTERS, 2006, 8 (06) :1045-1048
[9]   Radical cyclization approach to spirocyclohexadienones [J].
de Turiso, FGL ;
Curran, DP .
ORGANIC LETTERS, 2005, 7 (01) :151-154
[10]   Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant [J].
Dohi, T ;
Maruyama, A ;
Yoshimura, M ;
Morimoto, K ;
Tohma, H ;
Kita, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6193-6196