Rhodium-catalyzed ring opening of vinyl epoxides with alcohols and aromatic amines

被引:100
作者
Fagnou, K [1 ]
Lautens, M [1 ]
机构
[1] Univ Toronto, Dept Chem, Lash Miller Labs, Toronto, ON M5H 3H6, Canada
关键词
D O I
10.1021/ol0060782
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] [Rh(CO)(2)Cl](2) is an effective catalyst for the ring opening of vinyl epoxides with alcohols and aromatic amines under neutral conditions at room temperature. The reaction occurs with excellent diastereo- and regioselectivity (>20:1) giving the trans-1,2-amino alcohols or alkoxy alcohols for a wide range of substrates. The regio- and stereochemistry of these reactions is complementary to that typically obtained with palladium-catalyzed ring openings of vinyl epoxides.
引用
收藏
页码:2319 / 2321
页数:3
相关论文
共 23 条
[1]   METAL-SALTS AS NEW CATALYSTS FOR MILD AND EFFICIENT AMINOLYSIS OF OXIRANES [J].
CHINI, M ;
CROTTI, P ;
MACCHIA, F .
TETRAHEDRON LETTERS, 1990, 31 (32) :4661-4664
[2]   Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].
Evans, PA ;
Nelson, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582
[3]   Regioselective and enantiospecific rhodium-catalyzed intermolecular allylic etherification with ortho-substituted phenols [J].
Evans, PA ;
Leahy, DK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :5012-5013
[4]   Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction [J].
Evans, PA ;
Robinson, JE ;
Nelson, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6761-6762
[5]  
FIORENZA M, 1983, SYNTHESIS-STUTTGART, P640
[6]   A regio- and stereoselective synthesis of beta-amino alcohols [J].
Fu, XL ;
Wu, SH .
SYNTHETIC COMMUNICATIONS, 1997, 27 (10) :1677-1683
[7]   AN UNUSUAL CHEMOSELECTIVITY IN COBALT(II) CHLORIDE CATALYZED CLEAVAGE OF OXIRANES WITH ANILINES - A HIGHLY REGIOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS [J].
IQBAL, J ;
PANDEY, A .
TETRAHEDRON LETTERS, 1990, 31 (04) :575-576
[8]   Allylic amination [J].
Johannsen, M ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (04) :1689-1708
[9]   ORGANOTIN NUCLEOPHILES .6. PALLADIUM-CATALYZED ALLYLIC ETHERIFICATION WITH TIN ALKOXIDES [J].
KEINAN, E ;
SAHAI, M ;
ROTH, Z ;
NUDELMAN, A ;
HERZIG, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3558-3566
[10]   Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with phenols [J].
Lautens, M ;
Fagnou, K ;
Taylor, M .
ORGANIC LETTERS, 2000, 2 (12) :1677-1679