Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α, β-unsaturated ketones

Y Sugawara, W Yamada, S Yoshida…

Index: Sugawara, Yudai; Yamada, Wataru; Yoshida, Shunsuke; Ikeno, Taketo; Yamada, Tohru Journal of the American Chemical Society, 2007 , vol. 129, # 43 p. 12902 - 12903

Full Text: HTML

Citation Number: 67

Abstract

In the presence of a catalytic amount of a silver salt with DBU under a CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α, β-unsaturated carbonyl compounds in high yield. An isotopic experiment using C18O2 revealed that carbon dioxide mediated the rearrangement via an intramolecular nucleophilic attack on the alkyne activated by the silver catalyst.

Related Articles:

Diastereoselective Nucleophilic Addition to Aldehydes with Polar α??and α, β??Substituents

[Borg, Tessie; Danielsson, Jakob; Mohiti, Maziar; Restorp, Per; Somfai, Peter Advanced Synthesis and Catalysis, 2011 , vol. 353, # 11-12 p. 2022 - 2036]

Iterative approach to polyketide-type structures: stereoselective synthesis of 1, 3-polyols utilizing the catalytic asymmetric Overman esterification

[Binder, Joerg T.; Kirsch, Stefan F. Chemical Communications, 2007 , # 40 p. 4164 - 4166]

Gold??and Silver??Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives

[Pennell, Matthew N.; Turner, Peter G.; Sheppard, Tom D. Chemistry - A European Journal, 2012 , vol. 18, # 15 p. 4748 - 4758]

Enantioselective total synthesis of both the stereoisomers of dihydrokawain-5-ol

[Kamal, Ahmed; Krishnaji, Tadiparthi; Reddy, P. Venkat Tetrahedron Asymmetry, 2007 , vol. 18, # 15 p. 1775 - 1779]

“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

[Wang, Peng; Liu, Chun-Rong; Sun, Xiu-Li; Chen, Shuai-Shuai; Li, Jun-Fang; Xie, Zuowei; Tang, Yong Chemical Communications, 2012 , vol. 48, # 2 p. 290 - 292]

More Articles...