Merging chiral organocatalysts: enantio- and diastereoselective direct vinylogous Mannich reaction of alkylimines

被引:35
作者
Xiong, Xiao-Feng [1 ]
Jia, Zhi-Jun [1 ]
Du, Wei [1 ]
Jiang, Kun [1 ]
Liu, Tian-Yu [1 ]
Chen, Ying-Chun [1 ,2 ]
机构
[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Key Lab Drug Targeting & Drug Delivery Syst Educ, Chengdu 610041, Peoples R China
[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
关键词
DIVERSITY-ORIENTED SYNTHESIS; ASYMMETRIC ALDOL ADDITIONS; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; HIGHLY EFFICIENT; REVERSAL; IMINES; CYCLOADDITION; DERIVATIVES; COMPLEXES;
D O I
10.1039/b917408g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantio-and diastereoselective direct vinylogous Mannich reaction of alpha, alpha-dicyanoolefins and N-sulfonyl alkylimines has been developed by the catalysis of a new family of bifunctional organocatalysts merging chiral BINOL and 9-amino-9-deoxyepicinchona alkaloid skeletons, from which chiral beta-, delta- or gamma-amino compounds could be efficiently derived.
引用
收藏
页码:6994 / 6996
页数:3
相关论文
共 36 条
[1]   Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].
Akiyama, Takahiko ;
Honma, Yasuhiro ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402
[2]   Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity [J].
Arseniyadis, S ;
Valleix, A ;
Wagner, A ;
Mioskowski, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3314-3317
[3]   Solvent-controlled diastereoselective synthesis of cyclopentane derivatives by a [3+2] cyclization reaction of α,β-disubstituted (alkenyl)(methoxy)carbene complexes with methyl ketone lithium enolates [J].
Barluenga, J ;
Alonso, J ;
Fañanás, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2610-2616
[4]   A planning strategy for diversity-oriented synthesis [J].
Burke, MD ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58
[5]   A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions [J].
Carswell, Emma L. ;
Snapper, Marc L. ;
Hoveyda, Amir H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7230-7233
[6]   Rational combination of two privileged chiral backbones: Highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones [J].
Chen, Jia-Rong ;
An, Xiao-Lei ;
Zhu, Xiao-Yu ;
Wang, Xu-Fan ;
Xiao, Wen-Jing .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6006-6009
[7]   α,α-Dicyanoalkenes: versatile vinylogous nucleophiles for organic synthesis [J].
Cui, Hai-Lei ;
Chen, Ying-Chun .
CHEMICAL COMMUNICATIONS, 2009, (30) :4479-4486
[8]   Dual Organocatalysis: Asymmetric Allylic-Allylic Alkylation of α,α-Dicyanoalkenes and Morita-Baylis-Hillman Carbonates [J].
Cui, Hai-Lei ;
Peng, Jing ;
Feng, Xin ;
Du, Wei ;
Jiang, Kun ;
Chen, Ying-Chun .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) :1574-1577
[9]   The chemistry of trichlorosilyl enolates .2. Highly-selective asymmetric aldol additions of ketone enolates [J].
Denmark, SE ;
Wong, KT ;
Stavenger, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2333-2334
[10]   C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters [J].
Evans, DA ;
MacMillan, DWC ;
Campos, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10859-10860