Chiral N-phosphonyl imine chemistry:: new reagents and their applications for asymmetric reactions

被引:72
作者
Kattuboina, Adiseshu [1 ]
Li, Guigen [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
phosphoramide; N-phosphonyl imines; aziridine; aza-Darzens reaction; aza-Henry reaction; C(2)-symmetric diamine;
D O I
10.1016/j.tetlet.2008.01.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C(2)-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1573 / 1577
页数:5
相关论文
共 45 条
[31]   Chiral non-racemic sulfinimines: versatile reagents for asymmetric synthesis [J].
Morton, Daniel ;
Stockman, Robert A. .
TETRAHEDRON, 2006, 62 (38) :8869-8905
[32]   N,N-Dichloro-2-nitrobenzenesulfonamide as the electrophilic nitrogen source for direct diamination of enones [J].
Pei, W ;
Wei, HX ;
Chen, DJ ;
Headley, AD ;
Li, GG .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8404-8408
[33]  
Ruano JLG, 1996, TETRAHEDRON-ASYMMETR, V7, P3407
[34]  
Senanayake CH, 2005, ALDRICHIM ACTA, V38, P93
[35]   Enantioselective organocatalytic reductive amination [J].
Storer, RI ;
Carrera, DE ;
Ni, Y ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :84-86
[36]   Room-temperature highly diastereoselective Zn-mediated allylation of chiral N-tert-butanesulfinyl imines:: Remarkable reaction condition controlled stereoselectivity reversal [J].
Sun, Xing-Wen ;
Xu, Ming-Hua ;
Lin, Guo-Qiang .
ORGANIC LETTERS, 2006, 8 (21) :4979-4982
[37]   Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates.: Part 1:: Formation of cis-aziridines [J].
Sweeney, JB ;
Cantrill, AA ;
McLaren, AB ;
Thobhani, S .
TETRAHEDRON, 2006, 62 (15) :3681-3693
[38]   Nitrile biotransformations for the efficient synthesis of highly enantiopure 1-arylaziridine-2-carboxylic acid derivatives and their stereoselective ring-opening reactions [J].
Wang, Jin-Yuan ;
Wang, De-Xian ;
Zheng, Qi-Yu ;
Huang, Zhi-Tang ;
Wang, Mei-Xiang .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :2040-2045
[39]   Asymmetric synthesis of β-monosubstituted and β,β-disubstituted N-(p-toluenesulfinyl)-α-(aminoalkyl)acrylates via anionic additions of (α-carbalkoxyvinyl)cuprates to thiooxime S-oxides [J].
Wei, HX ;
Hook, JD ;
Fitzgerald, KA ;
Li, GG .
TETRAHEDRON-ASYMMETRY, 1999, 10 (04) :661-665
[40]   Diastereoselective and enantioselective Rh(l)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines [J].
Weix, DJ ;
Shi, YL ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1092-1093