A Secondary Amine Amide Organocatalyst for the Asymmetric Nitroaldol Reaction of α-Ketophosphonates

被引:51
作者
Chen, Xiaohong [1 ]
Wang, Jun [1 ]
Zhu, Yin [1 ]
Shang, Deju [1 ]
Gao, Bo [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ,2 ]
Su, Zhishan [1 ]
Hu, Changwei [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu, Peoples R China
[2] Sichuan Univ, State Key Lab Oral Dis, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
aldol reaction; amides; amines; Henry reaction; organocatalysis;
D O I
10.1002/chem.200801958
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A study was conducted for the asymmetric nitroaldol reaction of α-ketophosphonates by using a secondary amine amide organocatalyst. The study used a series of chiral secondary amine amides and synthesized it with α-ketophosphonates with nitromethane used as the solvent at 0°C. The nitroaldol reaction can be used for preparing nitrogen-containing compounds in the organic synthesis. It was observed during the study the α- ketophosphonates can be converted into optically active β-amino-α- hydroxy phosphonates, that further can be used as biological activity intermediates for inhibition of renin of HIV protease. The study also found that secondary amines like diethylamine or piperidine can promote the nitroaldol reaction of α-ketophosphonate at 0°C.
引用
收藏
页码:10896 / 10899
页数:4
相关论文
共 53 条
[1]  
[Anonymous], 2006, ANGEW CHEM, V118, P1550
[2]  
[Anonymous], COMPREHENSIVE ASYMME
[3]   Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(II)-iminopyridine complexes [J].
Blay, Gonzalo ;
Hernandez-Olmos, Victor ;
Pedro, Jose R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (03) :468-476
[4]   Catalytic asymmetric Henry reaction [J].
Boruwa, Joshodeep ;
Gogoi, Naminita ;
Saikia, Partha Pratim ;
Barua, Nabin C. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3315-3326
[5]   Nanocrystalline MgO for asymmetric Henry and Michael reactions [J].
Choudary, BM ;
Ranganath, KVS ;
Pal, U ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13167-13171
[6]   Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4875-4881
[7]   Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2001, (21) :2222-2223
[8]   NEW INHIBITORS OF RENIN THAT CONTAIN NOVEL PHOSPHOSTATINE LEU-VAL REPLACEMENTS [J].
DELLARIA, JF ;
MAKI, RG ;
STEIN, HH ;
COHEN, J ;
WHITTERN, D ;
MARSH, K ;
HOFFMAN, DJ ;
PLATTNER, JJ ;
PERUN, TJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :534-542
[9]   Asymmetric Henry reaction catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes:: Metal-controlled reversal of enantioselectivity [J].
Du, DM ;
Lu, SF ;
Fang, T ;
Xu, JX .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3712-3715
[10]   A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].
Evans, DA ;
Seidel, D ;
Rueping, M ;
Lam, HW ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693