Issue 25, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Feb 2012
Accepted
27 Mar 2012
First published
30 Apr 2012

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

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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