Rhodium-catalyzed asymmetric 1,6-addition of aryl zinc reagents to dienones

被引:95
作者
Hayashi, T [1 ]
Yamamoto, S [1 ]
Tokunaga, N [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
1,6-addition; asymmetric catalysis; organometallic reagents; rhodium; zinc;
D O I
10.1002/anie.200500678
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A highly enantioselective methodology allows the preparation of α,β-unsaturated ketones that contain a new stereogenic center at the C5 position. This approach is realized through the title reaction in the presence of chlorotrimethylsilane as a Lewis acid and a rhodium/(S)-binap complex as the catalyst followed by acidic hydrolysis (see scheme). binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4224 / 4227
页数:4
相关论文
共 68 条
[61]   Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds [J].
Shintani, R ;
Ueyama, K ;
Yamada, I ;
Hayashi, T .
ORGANIC LETTERS, 2004, 6 (19) :3425-3427
[62]   A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: Addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones [J].
Shintani, R ;
Tokunaga, N ;
Doi, H ;
Hayashi, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6240-6241
[63]  
Sibi MP, 2000, TETRAHEDRON, V56, P8033
[64]   Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones [J].
Takaya, Y ;
Ogasawara, M ;
Hayashi, T ;
Sakai, M ;
Miyaura, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5579-5580
[65]   Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to α,β-unsaturated ketones [J].
Tokunaga, N ;
Yoshida, K ;
Hayashi, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5445-5449
[66]  
Tomioka K., 1999, COMPREHENSIVE ASYMME, V3
[67]   Preparative and mechanistic studies on copper-mediated 1,6-addition reactions to a 2,4-dienone [J].
Uerdingen, M ;
Krause, N .
TETRAHEDRON, 2000, 56 (18) :2799-2804
[68]   A new cine-substitution of alkenyl Sulfones with aryltitanium reagents catalyzed by rhodium: Mechanistic studies and catalytic asymmetric synthesis of allylarenes [J].
Yoshida, K ;
Hayashi, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2872-2873