Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et2AlCN using amino alcohols and BINOLs as catalysts

被引:68
作者
Kaur, Parminder [1 ]
Pindi, Suresh [1 ]
Wever, Walter [1 ]
Rajale, Trideep [1 ]
Li, Guigen [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
MANNICH REACTIONS; DERIVATIVES; NITRILES; PROLINE; CYANIDE; AMIDES;
D O I
10.1039/c0cc00287a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines with Et2AlCN has been established. Both free amino alcohols and BINOLs have been proven to be effective catalysts to afford excellent enantioselectivities and yields. The N-phosphonyl group can be readily cleaved under mild conditions and enable purification of crude products by simple washing with hexane. The cleaved N,N-dialkyl diamine auxiliary can be recovered quantitatively via n-BuOH extraction. The scope for both N-phosphonyl imines and catalysts was vastly studied for this new catalytic system.
引用
收藏
页码:4330 / 4332
页数:3
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共 30 条
[1]   Dual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-quinolinolato) Aluminum Complex [J].
Abell, Joshua P. ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) :15118-+
[2]   Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional β-isocupreidine derivatives [J].
Abermil, Nacim ;
Masson, Geraldine ;
Zhu, Jieping .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) :12596-+
[3]   Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols [J].
Benedetti, F ;
Berti, F ;
Norbedo, S .
TETRAHEDRON LETTERS, 1999, 40 (05) :1041-1044
[4]   Expedient synthesis of chiral 1,2- and 1,4-diamines: Protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions [J].
Chowdari, Naidu S. ;
Ahmad, Moballigh ;
Albertshofer, Klaus ;
Tanaka, Fujie ;
Barbas, Carlos F., III .
ORGANIC LETTERS, 2006, 8 (13) :2839-2842
[5]   Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst [J].
Corey, EJ ;
Grogan, MJ .
ORGANIC LETTERS, 1999, 1 (01) :157-160
[6]   Pyridylalanine (Pal)-Peptide Catalyzed Enantioselective Allenoate Additions to N-Acyl Imines [J].
Cowen, Bryan J. ;
Saunders, Lindsey B. ;
Miller, Scott J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6105-+
[7]   Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives [J].
Davis, FA ;
Zhang, HM ;
Lee, SH .
ORGANIC LETTERS, 2001, 3 (05) :759-762
[8]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638
[9]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[10]   The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands [J].
Fu, Gregory C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1555-1564