Stereoselective Synthesis of Monofluoroalkyl α,β-Unsaturated Ketones From Allenyl Carbinol Esters Mediated by Gold and Selectfluor

被引：31

作者：

Jin, Zhuang ^{[1
]}

Hidinger, Rachel S. ^{[1
]}

Xu, Bo ^{[1
]}

Hammond, Gerald B. ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期

基金：

美国国家科学基金会;

关键词：

ENAMINE PHOSPHONATES; ANALOGS; REAGENT; COMPLEXES; ALDEHYDES; IMINES; AMINES;

D O I：

10.1021/jo301239p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allenyl carbinol ester 3 isomerizes to an E,Z mixture of the corresponding diene 2 in the presence of gold catalyst 4, but the resulting mixture yields monofluoroallcyl alpha,beta-unsaturated ketone 1 with exclusive E selectivity and in high yields after reaction with Selectfluor.

引用

收藏

页码：7725 / 7729

页数：5

相关论文

共 34 条

[1] PdII-catalyzed domino heterocyclization/cross-coupling of α-allenols and α-allenic esters:: Efficient preparation of functionalized buta-1,3-dienyl dihydrofurans [J].

Alcaide, Benito ;

Almendros, Pedro ;

del Campo, Teresa Martinez ;

Carrascosa, Rocio .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (07) :1140-1145

[2] Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties [J].

Arthurs, Claire L. ;

Wind, Natasha S. ;

Whitehead, Roger C. ;

Stratford, Ian J. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) :553-557

[3] ORGANIC FLUORINE COMPOUNDS .9. THE PREPARATION OF FLUOROACETONE AND 1-3-DIFLUOROACETONE [J].

BERGMANN, ED ;

COHEN, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (JUN) :2259-2262

[4] The synthesis of 1-fluoro- and 1,1-difluoro- analogues of 1-deoxy-D-xylulose [J].

Bouvet, D ;

O'Hagan, D .

TETRAHEDRON, 1999, 55 (34) :10481-10486

[5]

BRAVO P, 1989, J CHEM RES-S, P134

[6] Chemo-enzymatic synthesis of fluorinated sugar nucleotide:: Useful mechanistic probes for glycosyltransferases [J].

Burkart, MD ;

Vincent, SP ;

Düffels, A ;

Murray, BW ;

Ley, SV ;

Wong, CH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :1937-1946

[7] Gold(I)-catalyzed isomerization of allenyl carbinol esters: An efficient access to functionalized 1,3-butadien-2-ol esters [J].

Buzas, Andrea K. ;

Istrate, Florin M. ;

Gagosz, Fabien .

ORGANIC LETTERS, 2007, 9 (06) :985-988

[8]

CHAABOUNI MM, 1989, B SOC CHIM FR, P549

[9] RECHERCHES SUR LA FORMATION ET LA TRANSFORMATION DE DERIVES ORGANIQUES DU FLUOR .2. SUR LA SYNTHESE ET LESTERIFICATION DAMINO-ALCOOLS FLUORES [J].

CHERBULIEZ, E ;

YAZGI, A ;

RABINOWITZ, J .

HELVETICA CHIMICA ACTA, 1960, 43 (04) :1135-1142

[10] Lewis acid promoted aldol reaction of fluorinated silyl enol ethers from new fluoroacetylsilane derivatives [J].

Chung, WJ ;

Ngo, SC ;

Higashiya, S ;

Welch, JT .

TETRAHEDRON LETTERS, 2004, 45 (28) :5403-5406

← 1 2 3 4 →