ON THE ASYMMETRIC RH(I) CATALYZED [4+2] CYCLOISOMERIZATION REACTION - ELECTRONIC AND TORSIONAL LIGAND CONTROL OF ABSOLUTE STEREOSELECTION

被引:117
作者
MCKINSTRY, L [1 ]
LIVINGHOUSE, T [1 ]
机构
[1] MONTANA STATE UNIV,DEPT CHEM & BIOCHEM,BOZEMAN,MT 59717
关键词
D O I
10.1016/S0040-4020(01)80636-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of bisphosphine ligands related to DIOP as chiral modifiers in the Rh(I) catalyzed [4+2] cycloisomerization reaction results in moderate to good levels of enantioselection. The mode of absolute stereoinduction is subject to electronic and torsional modification of the chelating ligand.
引用
收藏
页码:6145 / 6154
页数:10
相关论文
共 22 条
[1]   CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES [J].
BEDNARSKI, M ;
MARING, C ;
DANISHEFSKY, S .
TETRAHEDRON LETTERS, 1983, 24 (33) :3451-3454
[2]   ON THE INTERACTIVITY OF CHIRAL AUXILIARIES WITH CHIRAL CATALYSTS IN THE HETERO DIELS-ALDER REACTION - A NEW ROUTE TO L-GLYCOLIPIDS [J].
BEDNARSKI, M ;
DANISHEFSKY, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6968-6969
[3]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[6]   ASYMMETRIC HYDROFORMYLATION OF VINYL-ACETATE WITH DIOP-TYPE LIGANDS [J].
HOBBS, CF ;
KNOWLES, WS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4422-4427
[7]  
HOBBS CH, COMMUNICATION
[8]   ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION CATALYZED BY THE CHIRAL TITANIUM REAGENT [J].
IWASAWA, N ;
SUGIMORI, J ;
KAWASE, Y ;
NARASAKA, K .
CHEMISTRY LETTERS, 1989, (11) :1947-1950
[9]   NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].
JOLLY, RS ;
LUEDTKE, G ;
SHEEHAN, D ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966
[10]   CHIRAL RECOGNITION IN CATALYTIC-HYDROGENATION OF ALPHA-ACYLAMINOACRYLIC ACIDS BY CATIONIC RHODIUM(I) COMPLEXES OF CHIRAL AMINOPHOSPHINES DERIVED FROM (R,R)-1,2-CYCLOHEXANEDIAMINE OR (R)-1,2-PROPANEDIAMINE [J].
KASHIWABARA, K ;
HANAKI, K ;
FUJITA, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (08) :2275-2280