Studies of rhodium-catalyzed ring opening of vinyl epoxides

被引:28
作者
Ha, JD [1 ]
Shin, EY [1 ]
Kang, SK [1 ]
Ahn, JH [1 ]
Choi, JK [1 ]
机构
[1] Korea Res Inst Chem Technol, Med Sci Div, Taejon 305600, South Korea
关键词
6-endo; vinyl epoxide; rhodium-catalyzed;
D O I
10.1016/j.tetlet.2004.03.137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective 6-endo mode cyclization of vinyl epoxides has been achieved by the use of a catalytic amount of [Rh(CO)(2)Cl](2) affording six-membered heterocycle systems, such as piperidines and tetrahydropyrans. The scope and limitations of the reaction are discussed. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4193 / 4195
页数:3
相关论文
共 26 条
[1]  
ABE H, 1980, SYNTHESIS-STUTTGART, P872
[2]  
ASHWORTH RW, 1977, TETRAHEDRON LETT, P339
[3]  
BOIUIN TLB, 1987, TETRAHEDRON, V43, P3309
[4]   SYNTHETIC APPROACHES TO STEREOISOMERS AND ANALOGS OF CASTANOSPERMINE [J].
BURGESS, K ;
HENDERSON, I .
TETRAHEDRON, 1992, 48 (20) :4045-4066
[5]   Synthetic methods for the stereoisomers of swainsonine and its analogues [J].
El Nemr, A .
TETRAHEDRON, 2000, 56 (44) :8579-8629
[6]   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
[7]   Rhodium-catalyzed ring opening of vinyl epoxides with alcohols and aromatic amines [J].
Fagnou, K ;
Lautens, M .
ORGANIC LETTERS, 2000, 2 (15) :2319-2321
[8]   MARINE NATURAL-PRODUCTS [J].
FAULKNER, DJ .
NATURAL PRODUCT REPORTS, 1986, 3 (01) :1-33
[9]  
HA JD, 2000, B KOR CHEM SOC, V24, P1567
[10]  
HOGEVEEN H, 1973, TETRAHEDRON LETT, P3671