Recyclable heterogeneous gold(i)-catalyzed oxidative ring expansion of alkynyl quinols: a practical access to tropone and its analogues

2021 ◽  
Author(s):  
Yingying Du ◽  
Bin Huang ◽  
Jiajun Zeng ◽  
Mingzhong Cai
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

A recyclable gold(i)-catalyzed oxidative ring expansion of alkynyl quinols for the construction of tropone and its analogues has been described.

The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

1998 ◽  
Vol 39 (8) ◽  
pp. 881-884 ◽  
Author(s):  
Christopher D. Gabbutt ◽  
John D. Hepworth ◽  
B. Mark Heron ◽  
Jean-Luc Thomas
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

Oxidative ring-expansion of benzothiazolines into 1,4-benzothiazines

1981 ◽  
Vol 18 (2) ◽  
pp. 279-282 ◽  
Author(s):  
Gaetano Liso ◽  
Giuseppe Trapani ◽  
Andrea Latrofa ◽  
Paolo Marchini
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furylsulfonamides and N→O Sulfonyl Transfer.

ChemInform ◽  
2007 ◽  
Vol 38 (34) ◽  
Author(s):  
Robert Hodgson ◽  
Andrew Kennedy ◽  
Adam Nelson ◽  
Alexis Perry
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

ChemInform Abstract: Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring Expansion of Alkynyl Quinols.

ChemInform ◽  
2016 ◽  
Vol 47 (17) ◽  
Author(s):  
Jidong Zhao ◽  
Jun Liu ◽  
Xin Xie ◽  
Shi Li ◽  
Yuanhong Liu
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

Preparation of oxonanes and azonanes by oxidative ring expansion: synthesis of obtusan

1995 ◽  
pp. 1137 ◽  
Author(s):  
David S. Brown ◽  
Mark C. Elliott ◽  
Christopher J. Moody ◽  
Timothy J. Mowlem
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

scholarly journals Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes

2020 ◽  
Author(s):  
María Martín López Martín López ◽  
Nicolas Jamey ◽  
Alexis Pinet ◽  
Bruno Figadère ◽  
Ferrié Laurent
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Ring Expansion ◽  
Alkoxy Radical ◽  
Tertiary Alcohols ◽  
Radical Traps ◽  
Oxidative Ring Expansion

Cyclobutanols undergo an oxidative ring expansion into 1,2-dioxanols by using Co(acac)<sub>2</sub> and triplet oxygen (<sup>3</sup>O<sub>2</sub>) as radical promoters. The formation of an alkoxy radical drives to the regioselective break of the strained ring with stabilization of a new radical on the most substituted side. The radical traps then oxygen to form 1,2-dioxanols. The reaction is particularly effective on secondary cyclobutanols but can work also on tertiary alcohols. Further acetylation generates peroxycarbenium species under catalytic Lewis acid conditions, which react with neutral nucleophiles. Many original 1,2-dioxanes, which would be difficult to prepare by another method, were then obtained with a preferred 3,6-<i>cis</i>-configuration. This method provides an interesting access to the total synthesis of many natural endoperoxides.

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