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
[1]   Copper-catalyzed tandem conjugate addition-electrophilic trapping: Ketones, esters, and nitriles as terminal electrophiles [J].
Agapiou, K ;
Cauble, DF ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4528-4529
[2]  
Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[3]  
Amengual R, 2002, SYNLETT, P1791
[4]  
[Anonymous], 2000, CATALYTIC ASYMMETRIC
[5]   Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal [J].
Arnold, LA ;
Naasz, R ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5841-5842
[6]   A rapid catalytic asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines [J].
Belyk, KM ;
Beguin, CD ;
Palucki, M ;
Grinberg, N ;
DaSilva, J ;
Askin, D ;
Yasuda, N .
TETRAHEDRON LETTERS, 2004, 45 (16) :3265-3268
[7]   Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aidol cyclization [J].
Bocknack, BM ;
Wang, LC ;
Krische, MJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5421-5424
[8]   High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites [J].
Boiteau, JG ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9481-9484
[9]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands [J].
Boiteau, JG ;
Imbos, F ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (05) :681-684
[10]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands (vol 5, pg 682, 2003) [J].
Boiteau, JG ;
Imbos, R ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (08) :1385-1385