Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity†‡

Hua Yang,a   Somdev Banerjeeb  and  Rich G. Carter*b  

* Corresponding authors

a College of Chemistry & Chemical Engineering, Central South University, Changsha, Hunan 410083, China

b Department of Chemistry, Oregon State University, Corvallis, OR 97331, US
E-mail: rich.carter@oregonstate.edu
Fax: +1 541-737-2062
Tel: +1 541-737-9486

Abstract

The development of a proline sulphonamide-catalysed method for enantioselective and diastereoselective construction of functionalized cyclohexenones is described. Impact of catalyst structure as well as solvent effects and additives are explored. A significant substrate scope is demonstrated by variation of both the aldehyde and the enone components. Diastereoselective derivatization of the cyclohexenone scaffold illustrates its utility as a building block for chemical synthesis.

Graphical abstract: Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity

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Article information

DOI
https://doi.org/10.1039/C2OB25400J
Article type
Paper
Submitted
24 Feb 2012
Accepted
27 Mar 2012
First published
30 Apr 2012

Org. Biomol. Chem., 2012,10, 4851-4863

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Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity

H. Yang, S. Banerjee and R. G. Carter, Org. Biomol. Chem., 2012, 10, 4851 DOI: 10.1039/C2OB25400J

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