The Meyer-Schuster rearrangement of ethoxyalkynyl carbinols

被引:58
作者
Lopez, Susana S. [1 ]
Engel, Douglas A. [1 ]
Dudley, Gregory B. [1 ]
机构
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
关键词
Meyer-Schuster; gold; alkoxyacetylene; propargyl alcohol; rearrangement;
D O I
10.1055/s-2007-973885
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of electron-rich alkoxyacetylenes and cationic gold catalysts provides excellent reactivity for the Meyer-Schuster rearrangement under mild conditions. Optimization of the reaction conditions with respect to stereoselectivity and investigations into the scope and mechanism of the rearrangement of secondary ethoxyalkynyl carbinols (gamma-ethoxy-substituted propargyl alcohols) to alpha,beta-unsaturated esters are described.
引用
收藏
页码:949 / 953
页数:5
相关论文
共 39 条
[31]  
Stang P.J., 1995, MODERN ACETYLENE CHE
[32]   Au- and Pt-catalyzed cycloisomerizations of 1,5-enynes to cyclohexadienes with a broad alkyne scope [J].
Sun, Jianwei ;
Conley, Matthew P. ;
Zhang, Liming ;
Kozmin, Sergey A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9705-9710
[33]   RUPE AND MEYER-SCHUSTER REARRANGEMENTS [J].
SWAMINATHAN, S ;
NARAYANAN, KV .
CHEMICAL REVIEWS, 1971, 71 (05) :429-+
[34]   Gold-catalyzed efficient formation of alkenyl enol esters/carbonates from trimethylsilylmethyl-substituted propargyl esters/carbonates [J].
Wang, Shaozhong ;
Zhang, Liming .
ORGANIC LETTERS, 2006, 8 (20) :4585-4587
[35]   STEREOSELECTIVE TOTAL SYNTHESIS OF ANTIFUNGAL MOLD METABOLITE 7ALPHA-METHOXY-3A, 10B-DIMETHYL-1,2,3,3AALPHA, 5AALPHA, 7, 10BBETA, 10CALPHA-OCTAHYDRO-4H, 9H-FURO[2',3',4'-4,5]NAPTHO[2,1-C]PYRAN-4,10-DIONE [J].
WELCH, SC ;
HAGAN, CP ;
WHITE, DH ;
FLEMING, WP ;
TROTTER, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :549-556
[36]  
Yamamoto H., 2000, LEWIS ACIDS ORGANIC
[37]   MEYER-SCHUSTER REARRANGEMENT OF GAMMA-SULFUR-SUBSTITUTED PROPARGYL ALCOHOLS - A CONVENIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED THIOESTERS [J].
YOSHIMATSU, M ;
NAITO, M ;
KAWAHIGASHI, M ;
SHIMIZU, H ;
KATAOKA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4798-4802
[38]  
YU M, 2007, IN PRESS ADV SYNTH C
[39]   Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes [J].
Zhang, LM ;
Kozmin, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11806-11807