Issue 15, 2009
From the journal:

Organic & Biomolecular Chemistry

Enantioselective synthesis of highly functionalized octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehydes via organocatalytic domino reactions†‡

Bor-Cherng Hong,*a   Roshan Y. Nimjea  and  Ju-Hsiou Liaoa  

* Corresponding authors

a Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi 621, Taiwan, ROC
E-mail: chebch@ccu.edu.tw
Fax: +886 5 272104
Tel: +886 5 2428174

Abstract

Organocatalytic double Michael reaction and the subsequent aldol condensation of (E)-7-oxooct-5-enal and 3-arylpropenal (e.g., cinnamaldehyde) provided octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehyde in high diastereoselectivity and high enantioselectivity (>99% ee). Structures of the adducts 5a and 5j were confirmed unambiguously by X-ray analysis.

Graphical abstract: Enantioselective synthesis of highly functionalized octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehydes via organocatalytic domino reactions

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Article information

DOI
https://doi.org/10.1039/B906205J
Article type
Paper
Submitted
30 Mar 2009
Accepted
06 May 2009
First published
11 Jun 2009

Org. Biomol. Chem., 2009,7, 3095-3101

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Enantioselective synthesis of highly functionalized octahydro-6-oxo-1-phenylnaphthalene-2-carbaldehydes via organocatalytic domino reactions

B. Hong, R. Y. Nimje and J. Liao, Org. Biomol. Chem., 2009, 7, 3095 DOI: 10.1039/B906205J

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