ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION

被引:186
作者
CHINCHILLA, R [1 ]
NAJERA, C [1 ]
SANCHEZAGULLO, P [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN
关键词
D O I
10.1016/0957-4166(94)80183-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure guanidines with and without C-2 symmetry have been prepared and used as catalysts in the addition of nitromethane to aldehydes (Henry reaction). The influence of the structure and amount of the guanidine, the solvent and the temperature in the enantioselectivity of the nitroaldol reaction has also been studied.
引用
收藏
页码:1393 / 1402
页数:10
相关论文
共 27 条
[1]   DEPROTONATION OF NITROALKANES BY BICYCLIC AMIDINE AND GUANIDINE BASES - EVIDENCE FOR MOLECULAR RECOGNITION WITHIN A CATALYTIC CYCLE FOR C-C BOND FORMATION [J].
BOYLE, PH ;
CONVERY, MA ;
DAVIS, AP ;
HOSKEN, GD ;
MURRAY, BA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :239-242
[2]   KINETIC RESOLUTION OF RACEMIC CARBOXYLIC-ACIDS WITH HOMOCHIRAL ALCOHOLS AND DICYCLOHEXYLCARBODIIMIDE [J].
CHINCHILLA, R ;
NAJERA, C ;
YUS, M ;
HEUMANN, A .
TETRAHEDRON-ASYMMETRY, 1991, 2 (02) :101-104
[3]   KINETIC RESOLUTION OF RACEMIC ALCOHOLS WITH CHIRAL CARBOXYLIC-ACIDS AND DICYCLOHEXYLCARBODIIMIDE [J].
CHINCHILLA, R ;
NAJERA, C ;
YUS, M ;
HEUMANN, A .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :851-854
[4]   CHIRAL RECOGNITION OF AROMATIC CARBOXYLATE ANIONS BY AN OPTICALLY-ACTIVE ABIOTIC RECEPTOR CONTAINING A RIGID GUANIDINIUM BINDING SUBUNIT [J].
ECHAVARREN, A ;
GALAN, A ;
LEHN, JM ;
DEMENDOZA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4994-4995
[5]   SECRETIN .6. SIMULTANEOUS INSITU SYNTHESES OF 3 ANALOGS OF C-TERMINAL TRICOSAPEPTIDE AND A STUDY OF THEIR CONFORMATION [J].
FINK, ML ;
BODANSZKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (04) :974-977
[6]   STEREOSELECTIVE ADDITION OF NITROMETHANE TO LEVOGLUCOSENONE - FORMATION AND STRUCTURE OF 2/1 AND 1/2 ADDUCTS [J].
FORSYTH, AC ;
GOULD, RO ;
PATON, RM ;
SADLER, IH ;
WATT, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22) :2737-2741
[7]   HIGHLY SELECTIVE BASE-CATALYZED ADDITIONS OF NITROMETHANE TO LEVOGLUCOSENONE [J].
FORSYTH, AC ;
PATON, RM ;
WATT, I .
TETRAHEDRON LETTERS, 1989, 30 (08) :993-996
[8]   ENANTIODIFFERENTIATION OF CARBOXYLATES BY CHIRAL BUILDING-BLOCKS FOR ABIOTIC ANION RECEPTORS [J].
GLEICH, A ;
SCHMIDTCHEN, FP ;
MIKULCIK, P ;
MULLER, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :55-58
[10]   FLUORINATED LACTIC ACIDS - EASILY ACCESSIBLE REAGENTS FOR THE ANALYSIS OF CHIRAL COMPOUNDS BY F-19 NMR-SPECTROSCOPY - F-19 NMR SEPARATION OF THE 8 ISOMERS OF MENTHOL [J].
HEUMANN, A ;
FAURE, R .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1276-1279