Issue 36, 2010
From the journal:

Chemical Communications

Desymmetrizing asymmetric ring expansion: stereoselective synthesis of 7-membered cyclic β-ketocarbonyl compounds with an α-hydrogen†

Takuya Hashimoto,a   Yuki Naganawaa  and  Keiji Maruoka*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, Japan
E-mail: maruoka@kuchem.kyoto-u.ac.jp
Fax: +81 75-753-4041
Tel: +81 75-753-4041

Abstract

Ring expansion of symmetrically substituted cyclohexanones with N-α-diazoacetyl camphorsultam was devised as a stereoselective pathway to the functionalized 7-membered cyclic β-keto carbonyls having a kinetically stabilized α-hydrogen.

Graphical abstract: Desymmetrizing asymmetric ring expansion: stereoselective synthesis of 7-membered cyclic β-keto carbonyl compounds with an α-hydrogen

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Article information

DOI
https://doi.org/10.1039/C0CC01424A
Article type
Communication
Submitted
15 May 2010
Accepted
28 Jul 2010
First published
23 Aug 2010

Chem. Commun., 2010,46, 6810-6812

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Desymmetrizing asymmetric ring expansion: stereoselective synthesis of 7-membered cyclic β-keto carbonyl compounds with an α-hydrogen

T. Hashimoto, Y. Naganawa and K. Maruoka, Chem. Commun., 2010, 46, 6810 DOI: 10.1039/C0CC01424A

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