Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and base

被引：21

作者：

Magomedov, NA ^{[1
]}

Ruggiero, PL ^{[1
]}

Tang, YC ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 19期

关键词：

D O I：

10.1021/ol048545b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by a sterically demanding Lewis acid and an amine base have been accomplished under mild reaction conditions. The extension of this methodology to the synthesis of eight-membered rings is also demonstrated.

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页码：3373 / 3375

页数：3

相关论文

共 35 条

[1]

BRITTENKELLY M, 1980, SYNTHESIS-STUTTGART, P27

[2] MAJOR EFFECT OF THE LEAVING GROUP IN DIALKYLBORON CHLORIDES AND TRIFLATES IN CONTROLLING THE STEREOSPECIFIC CONVERSION OF KETONES INTO EITHER (E)-ENOL OR (Z)-ENOL BORINATES [J].

BROWN, HC ;

DHAR, RK ;

BAKSHI, RK ;

PANDIARAJAN, PK ;

SINGARAM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3441-3442

[3] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].

Crimmins, MT ;

King, BW ;

Tabet, EA ;

Chaudhary, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902

[4] Demonstrating the synergy of synthetic, mechanistic, and computational studies in a regioselective aniline synthesis [J].

Davies, IW ;

Marcoux, JF ;

Kuethe, JT ;

Lankshear, MD ;

Taylor, JDO ;

Tsou, N ;

Dormer, PG ;

Hughes, DL ;

Houk, KN ;

Guner, V .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1298-1308

[5] SPIRANES .3. SYNTHESIS OF POLYSPIRO COMPOUNDS CONSISTING OF CYCLOHEXANE RINGS [J].

DEJONGH, HAP ;

WYNBERG, H .

TETRAHEDRON, 1964, 20 (11) :2553-&

[6] X=Y-ZH systems as potential 1,3-dipoles. Part 57: Cascade 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone: remarkable rate enhancement and control of cycloaddition regiochemistry by Lewis acids [J].

Dunn, PJ ;

Graham, AB ;

Grigg, R ;

Higginson, P ;

Thornton-Pett, M .

TETRAHEDRON, 2002, 58 (38) :7727-7733

[7]

EVANS D A, 1978, Journal of the American Chemical Society, V100, P4593, DOI 10.1021/ja00482a045

[8] [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT [J].

EVANS, DA ;

GOLOB, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4765-4766

[9] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

VOGEL, E ;

NELSON, JV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) :6120-6123

[10] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

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