Catalytic Enantioselective α-Arylation of Carbonyl Compounds

被引:72
作者
Burtoloso, Antonio C. B. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Paulo, Brazil
关键词
enolates; alpha-arylation; carbonyl compounds; palladium; nickel; quaternary benzylic centers; ASYMMETRIC ARYLATION; RATE ACCELERATION; CARBENE LIGANDS; PALLADIUM; CONSTRUCTION; COMPLEXES; KETONES;
D O I
10.1055/s-0028-1087673
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective creation of benzylic quaternary centers still is a continuous challenge to many synthetic organic chemists. Among the existing methods for installation of this type of center, the direct asymmetric alpha-arylation of carbonyl compounds is very attractive due to the ready availability of the coupling substrates. Herein, we present some new tools to the catalytic asymmetric alpha-arylation of carbonyl compounds that overcame many of the drawbacks posted in previous methods for this type of reaction.
引用
收藏
页码:320 / 327
页数:8
相关论文
共 32 条
[1]   Enantioselective α-arylation of cyclohexanones with diaryl iodonium salts:: Application to the synthesis of (-)-epibatidine [J].
Aggarwal, VK ;
Olofsson, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5516-5519
[2]   Asymmetric arylation of ketone enolates [J].
Ahman, J ;
Wolfe, JP ;
Troutman, MV ;
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919
[3]   Asymmetric organocatalytic α-arylation of aldehydes [J].
Aleman, Jose ;
Cabrera, Silvia ;
Maerten, Eddy ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523
[4]   Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].
Aleman, Jose ;
Richter, Bo ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519
[5]   Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation [J].
Arao, Takafumi ;
Kondo, Kazuhiro ;
Aoyama, Toyohiko .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) :1743-1747
[6]   Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles [J].
Bella, M ;
Kobbelgaard, S ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3670-3671
[7]   RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION [J].
BUNCEL, E ;
DUST, JM ;
TERRIER, F .
CHEMICAL REVIEWS, 1995, 95 (07) :2261-2280
[8]   Nickel-catalyzed asymmetric α-arylation of ketone enolates [J].
Chen, GS ;
Kwong, FY ;
Chan, HO ;
Yu, WY ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2006, (13) :1413-1415
[9]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[10]  
2-V