A remarkable ene-like reaction: Development and synthetic applications

被引:24
作者
Ciufolini, MA
Deaton, MV
Zhu, SR
Chen, MY
机构
关键词
D O I
10.1016/S0040-4020(97)01016-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalytic ene-like reaction of aldehydes with those vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, is discussed in detail. The reaction is promoted by 0.05 eguiv. of the 1:1 complex of Yb(fod)(3) and acetic acid, and it is forms the centerpiece of our synthesis of chlorovulone II, mitomycinoids and phyllanthocin. (C) 1997 Elsevier Science Ltd.
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页码:16299 / 16312
页数:14
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共 74 条
[51]  
SHER F, 1973, TETRAHEDRON LETT, P577
[52]   LEWIS-ACID PROMOTED ENE-LIKE REACTIONS OF ENOL ETHERS WITH ALDEHYDES [J].
SHODA, H ;
NAKAMURA, T ;
TANINO, K ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1993, 34 (39) :6281-6284
[53]   SYNTHESIS AND REACTIONS OF SIMPLE 3(2H)-FURANONES [J].
SMITH, AB ;
LEVENBERG, PA ;
JERRIS, PJ ;
SCARBOROUGH, RM ;
WOVKULICH, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1501-1513
[54]   PHYLLANTHOSIDE PHYLLANTHOSTATIN SYNTHETIC STUDIES .7. TOTAL SYNTHESIS OF (+)-PHYLLANTHOCIN AND (+)-PHYLLANTHOCINDIOL [J].
SMITH, AB ;
FUKUI, M ;
VACCARO, HA ;
EMPFIELD, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2071-2092
[55]   TOTAL SYNTHESIS OF (+)-PHYLLANTHOCIN [J].
SMITH, AB ;
FUKUI, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1269-1272
[56]   PHYLLANTHOSIDE PHYLLANTHOSTATIN SYNTHETIC STUDIES .8. TOTAL SYNTHESIS OF (+)-PHYLLANTHOSIDE - DEVELOPMENT OF THE MITSUNOBU GLYCOSYL ESTER PROTOCOL [J].
SMITH, AB ;
RIVERO, RA ;
HALE, KJ ;
VACCARO, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2092-2112
[57]  
SMITH AB, 1991, J AM CHEM SOC, V109, P1272
[58]   DIAKLYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES - SYNTHESIS OF IPSENOL [J].
SNIDER, BB ;
RODINI, DJ .
TETRAHEDRON LETTERS, 1980, 21 (19) :1815-1818
[59]   DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES [J].
SNIDER, BB ;
RODINI, DJ ;
KIRK, TC ;
CORDOVA, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (02) :555-563
[60]   Synthesis of (+/-)-allocyathin B-2 and (+)-erinacine A [J].
Snider, BB ;
Vo, NH ;
ONeil, SV ;
Foxman, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7644-7645