Palladium-Catalyzed Asymmetric Dearomatization of Naphthalene Derivatives

被引:157
作者
Garcia-Fortanet, Jorge [1 ]
Kessler, Florian [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院;
关键词
ENANTIOSELECTIVE CONSTRUCTION; OXIDATIVE DEAROMATIZATION; BIRCH REDUCTION; ALKYLATION; ARENES;
D O I
10.1021/ja9025193
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An intramolecular enantioselective metal-catalyzed dearomatization reaction is described. This procedure allows the dearomatization of naphthalene derivatives through an electrophilic aromatic substitution-type reaction on a Pd(II) intermediate. The high yields and enantioselectivities achieved make this procedure a valuable method for synthetic chemists.
引用
收藏
页码:6676 / +
页数:3
相关论文
共 19 条
[1]   Additions to functionalized arenes with concurrent dearomatization [J].
Bach, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :729-730
[2]   Catalytic asymmetric vinylation of ketone enolates [J].
Chieffi, A ;
Kamikawa, K ;
Åhman, J ;
Fox, JM ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (12) :1897-1900
[3]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[4]  
2-V
[5]   A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols [J].
Dohi, Toshifumi ;
Maruyama, Akinobu ;
Takenaga, Naoko ;
Senami, Kento ;
Minamitsuji, Yutaka ;
Fujioka, Hiromichi ;
Caemmerer, Simon B. ;
Kita, Yasuyuki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3787-3790
[6]   Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].
Douglas, CJ ;
Overman, LE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367
[7]   Enantioselective construction of quaternary stereocenter through a reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: Efficient synthesis of various biologically significant compounds [J].
Funabashi, K ;
Ratni, H ;
Kanai, M ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10784-10785
[8]  
Harman WD, 2004, TOP ORGANOMETAL CHEM, V7, P95
[9]   PREPARATION AND REARRANGEMENT OF 6A-METHYL-6AH-BENZO[A]CARBAZOLE AND 11B-METHYL-11BH-BENZO[C]CARBAZOLE [J].
KULAGOWSKI, JJ ;
MOODY, CJ ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2733-2739
[10]   PREPARATION AND REARRANGEMENT OF 6A-METHYL-6AH-BENZO[A]CARBAZOLE AND 11B-METHYL-11BH-BENZO[C]CARBAZOLE [J].
KULAGOWSKI, JJ ;
MITCHELL, G ;
MOODY, CJ ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :650-651