DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF HOMOCHIRAL ALCOHOLS

被引:31
作者
ALLER, E [1 ]
COX, GG [1 ]
MILLER, DJ [1 ]
MOODY, CJ [1 ]
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)78227-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II) acetate catalysed decomposition of the phenyldiazoacetates 3 in the presence of alcohols (methanol, propan-2-ol, tert-butanol) led to the O-II insertion products 4-6 in varying yields; the diastercomeric excess of the product ranged from 5-53%.
引用
收藏
页码:5949 / 5952
页数:4
相关论文
共 15 条
[1]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[2]  
COX GG, 1992, SYNLETT, P975
[3]   CHEMOSELECTIVITY OF RHODIUM CARBENOIDS - A COMPARISON OF THE SELECTIVITY FOR O-H INSERTION REACTIONS OR CARBONYL YLIDE FORMATION VERSUS ALIPHATIC AND AROMATIC C-H INSERTION AND CYCLOPROPANATION [J].
COX, GG ;
MOODY, CJ ;
AUSTIN, DJ ;
PADWA, A .
TETRAHEDRON, 1993, 49 (23) :5109-5126
[4]   RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST [J].
COX, GG ;
MILLER, DJ ;
MOODY, CJ ;
SIE, ERHB ;
KULAGOWSKI, JJ .
TETRAHEDRON, 1994, 50 (10) :3195-3212
[5]   ALPHA-HYDROXY ESTERS AS CHIRAL AUXILIARIES IN ASYMMETRIC CYCLOPROPANATIONS BY RHODIUM(II)-STABILIZED VINYLCARBENOIDS [J].
DAVIES, HML ;
HUBY, NJS ;
CANTRELL, WR ;
OLIVE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9468-9479
[6]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[8]   SYNTHESIS AND CATALYTIC REACTIONS OF CHIRAL N-(DIAZOACETYL)OXAZOLIDONES [J].
DOYLE, MP ;
DOROW, RL ;
TERPSTRA, JW ;
RODENHOUSE, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1663-1666
[9]  
DOYLE MP, 1993, SYNLETT, P151
[10]  
MAAS G, 1987, TOP CURR CHEM, V137, P75