CYCLOADDITION OF ENAMINES WITH ALKYNYLPHOSPHONATES - A ROUTE TO FUNCTIONALIZED MEDIUM-SIZED RINGS

被引:27
作者
RUDER, SM
NORWOOD, BK
机构
[1] Department of Chemistry, Virginia Commonwealth University, Richmond
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)73213-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted seven and eight membered rings were formed from cyclopentanone and cyclohexanone via cycloadditions of pyrrolidine enamines with alkynyl phosphonates. This procedure provides straightforward access to functionalized medium sized rings that could be further manipulated in the synthesis of a number of natural products.
引用
收藏
页码:3473 / 3476
页数:4
相关论文
共 9 条
[1]   REACTION OF ENAMINES OF CYCLIC KETONES WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].
BERCHTOLD, GA ;
UHLIG, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1459-&
[2]   ENAMINE CHEMISTRY .6. REACTIONS WITH PROPIOLATES [J].
BRANNOCK, KC ;
BURPITT, RD ;
THWEATT, JG ;
GOODLETT, VW .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) :818-&
[3]   ENAMINE CHEMISTRY .2. REACTIONS WITH ACETYLENEDICARBOXYLATES [J].
BRANNOCK, KC ;
BURPITT, RD ;
THWEATT, JG ;
GOODLETT, VW .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1464-&
[4]  
CHATTHA MS, 1971, J ORG CHEM, V36, P2719
[5]   [2+2] CYCLOADDITION OF ETHYL PROPIOLATE AND SILYL ENOL ETHERS [J].
CLARK, RD ;
UNTCH, KG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) :248-253
[6]  
DARLING SD, 1975, TETRAHEDRON LETT, P3279
[7]   REACTIONS OF ACETYLENIC ESTERS WITH ENAMINES [J].
HUEBNER, CF ;
DORFMAN, L ;
DONOGHUE, E ;
STRACHAN, P ;
ROBISON, MM ;
PIERSON, WG .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11) :3134-&
[8]  
WADSWORTH WS, 1977, ORG REACTIONS, V25, pCH2
[9]  
1993, 205TH NAT ACS M DENV