NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - NEW REGIOSPECIFIC METHODOLOGY FOR THE SYNTHESIS OF ALPHA,BETA-UNSATURATED CYCLIC-KETONES

被引：21

作者：

MAGNUS, P

EVANS, A

LACOUR, J

机构：

[1] Department of Chemistry and Biochemistry, University of Texas at Austin, Austin

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 21期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)79564-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of TIPS enol ethers with PhIO/TMSN3 followed by desilylation/elimination with fluoride ion gives good yields of the alpha,beta-unsaturated ketone.

引用

页码：2933 / 2936

页数：4

共 14 条

[1] AN EFFICIENT AND SHORT DEGRADATION OF THE CHOLIC-ACID SIDE-CHAIN - A NEW METHOD FOR THE PREPARATION AND DEHYDROGENATION OF 4,5-DIHYDRO-OXAZOLES [J].

BARTON, DHR ;

MOTHERWELL, WB ;

WOZNIAK, J ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (09) :1865-1869

[2]

Buckle D. R., 1991, COMPREHENSIVE ORGANI, V7, P119

[3] MODERN ORGANOSELENIUM CHEMISTRY [J].

CLIVE, DLJ .

TETRAHEDRON, 1978, 34 (08) :1049-1132

[4] SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY PALLADIUM(II)-CATALYZED DEHYDROSILYLATION OF SILYL ENOL ETHERS [J].

ITO, Y ;

HIRAO, T ;

SAEGUSA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :1011-1013

[5] GENERAL AND EFFICIENT APPROACH TO SPIROCYCLOHEXADIENONES [J].

KANE, VV .

SYNTHETIC COMMUNICATIONS, 1976, 6 (03) :237-242

[6] NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - DIRECT BETA-AZIDO FUNCTIONALIZATION OF TRIISOPROPYLSILYL ENOL ETHERS [J].

MAGNUS, P ;

LACOUR, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :767-769

[7] STUDIES ON THE SYNTHESIS OF BATRACHOTOXIN [J].

MAGNUS, P ;

LEAPHEART, T ;

WALKER, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (17) :1185-1186

[8]

MAGNUS P, UNPUB J AM CHEM SOC

[9] ORGANOSELENIUM CHEMISTRY - CONVERSION OF KETONES TO ENONES BY SELENOXIDE SYN ELIMINATION [J].

REICH, HJ ;

RENGA, JM ;

REICH, IL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5434-5447

[10]

RINGOLD HJ, 1962, CHEM IND-LONDON, P211

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