A facile C-C bond cleavage in the epoxides and its use for the synthesis of oxygenated heterocycles by a ring expansion strategy

被引:21
作者
Lakshmipathi, P [1 ]
Grée, D [1 ]
Grée, R [1 ]
机构
[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6052, Lab Synth & Activat Biomol, F-35700 Rennes, France
关键词
D O I
10.1021/ol017164k
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
The bicyclic epoxy alcohols when treated with DAST gave a new class of rearranged organofluorine compounds, by a ring expansion via C-C bond cleavage of the oxirane ring. The outcome of this reaction with respect to ring size and stereochemical relation between the functionalities is presented here.
引用
收藏
页码:451 / 454
页数:4
相关论文
共 17 条
[1]
OXIRANYLCARBINYL REARRANGEMENT - THE EFFECT OF PRECURSOR STEREOCHEMISTRY [J].
CLARK, GR .
TETRAHEDRON LETTERS, 1984, 25 (27) :2839-2842
[2]
EVIDENCE FOR A CHANGE IN RATE-DETERMINING STEP IN ACID-CATALYZED HYDROLYSIS OF A VINYL ETHER [J].
COOPER, JD ;
VITULLO, VP ;
WHALEN, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (23) :6294-&
[3]
CORSER DA, 1992, SYNLETT, P987
[5]
Synthesis of the 9-fluoro analogues of disparlure [J].
Filmon, J ;
Grée, D ;
Grée, R .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) :271-273
[6]
Hudlicky M., 1988, ORG REACTIONS, V35, P513
[7]
Demonstration of reversible C-C bond cleavage in oxiranylcarbinyl radicals. [J].
Marples, BA ;
Rudderham, JA ;
Slawin, AMZ ;
Edwards, AJ ;
Hird, NW .
TETRAHEDRON LETTERS, 1997, 38 (20) :3599-3602
[8]
MORITA H, 1969, TETRAHEDRON LETT, P1347
[9]
PADWA A, 1984, 1 3 DIPOLAR CYCLOADD, V2, P341