The Retro-Michael Reaction of 1,5-Dicarbonyl Compounds: Scope and Limitation

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Title:The Retro-Michael Reaction of 1,5-Dicarbonyl Compounds: Scope and Limitation
Creators:
Wang, Jian-Xin
Li, Tong-Shuang
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 1, pp. 107-113
Uncontrolled Keywords:Tricyclic compounds, Retro-Michael reaction, Terpenoids, Steroids, Dicarbonyl compounds

Abstract

Under catalysis of NaOH or KOH adsorbed on glass wool and by using steam distillation, (20<i>R</i>,<i>S</i>)-4,4,5,14-tetramethyl-18,19-dinor-13,17-seco-5β,8α,9β,10α,14β-cholestane-13,17-dione (<strong>1</strong>) and 3,14-dioxo-14,15-seco-5α-cholestan-15-al (<strong>4</strong>) gave good yield (&gt;59%) of the corresponding tricyclic compounds (<strong>8a</strong>, <strong>8b</strong> and <strong>10a</strong>) <i>via</i> a retro-Michael reaction at 250 °C. While 5-oxo-4-nor-3,5-secocholestan-3-oic acid (<strong>6</strong>) and ethyl 5-oxo-4-nor-3,5-secocholestan-3-oate (<strong>7</strong>) afforded low yield (&lt;15%) of the retro-Michael cleavage products (<strong>12a</strong>, <strong>12b</strong>) at the same conditions. Thus, the retro-Michael reaction worked well for 1,5-diketones and 1,5-keto aldehydes but gave poor yield for 1,5-keto esters and 1,5-keto acids. <p>

Title:The Retro-Michael Reaction of 1,5-Dicarbonyl Compounds: Scope and Limitation
Creators:
Wang, Jian-Xin
Li, Tong-Shuang
Uncontrolled Keywords:Tricyclic compounds, Retro-Michael reaction, Terpenoids, Steroids, Dicarbonyl compounds
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:1
Page Range:pp. 107-113
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990107UNSPECIFIED
ID Code:1460
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Wang, Jian-Xin; Li, Tong-Shuang (1999) The Retro-Michael Reaction of 1,5-Dicarbonyl Compounds: Scope and Limitation. Collection of Czechoslovak Chemical Communications, 64 (1). pp. 107-113. ISSN 0010-0765

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