Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates

被引:74
作者
Choudhury, Abhijnan Ray [1 ]
Mukherjee, Santanu [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
PHOSPHONIC ACID-DERIVATIVES; HETEROBIMETALLIC LANTHANOID COMPLEXES; BOND-FORMING REACTIONS; C-H FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; AMINO PHOSPHONATES; STEREOSELECTIVE-SYNTHESIS; ISOTHIOCYANATO PHOSPHONATES; ANTIBACTERIAL AGENTS; ABRAMOV REACTION;
D O I
10.1039/c6sc02466a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantioselective dearomatization of isoquinolines has been developed using chiral anion-binding catalysis. This transformation, catalyzed by a simple and easy to prepare tert-leucine-based thiourea derivative, makes use of silyl phosphite as a nucleophile and generates cyclic alpha-aminophosphonates. This is the first time asymmetric anion-binding catalysis has been applied to the synthesis of alpha-aminophosphonates.
引用
收藏
页码:6940 / 6945
页数:6
相关论文
共 87 条
[1]   Catalytic enantioselective Pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex [J].
Abell, Joshua P. ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) :10521-+
[2]  
Abramov V.S., 1950, DOKL AKAD NAUK+, V73, P487
[3]  
Abramov V.S., 1954, DOKLAQLKD NAUK S S S, V95, P991
[4]   Catalytic Asymmetric Additions of Carbon-Centered Nucleophiles to Nitrogen-Containing Aromatic Heterocycles [J].
Ahamed, Muneer ;
Todd, Matthew. H. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (31) :5935-5942
[5]   Asymmetric Organocatalysis and the Nitro Group Functionality [J].
Aitken, Lewis S. ;
Arezki, Natasha R. ;
Dell'Isola, Antonio ;
Cobb, Alexander J. A. .
SYNTHESIS-STUTTGART, 2013, 45 (19) :2627-2648
[6]   Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[7]   Diastereoselective Synthesis of Enantiopure α-Aminophosphonic Acid Derivatives: Pudovik Reaction in Stereoselective Synthesis (Dedicated to A. N. Pudovik, 1916-2006) [J].
Alfonsov, V. A. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (11) :2637-2644
[8]   PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
NATURE, 1978, 272 (5648) :56-58
[9]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[10]   PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - RATIONALE, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
LAMBERT, RW ;
RINGROSE, PS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :677-683