Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective three-component reactions of aryldiazoacetates with alcohols/water and alkynals: application to substituted enelactones†

Xingchun Han,ab   Liqing Jiang,a   Min Tanga  and  Wenhao Hu*a  

* Corresponding authors

a Department of Chemistry, and Institute of Drug Discovery and Development, Shanghai Engineering Research Center for Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, P. R. China
E-mail: whu@chem.ecnu.edu.cn
Fax: +86-021-62233176

b Roche R&D Center (China) Ltd. Shanghai, China

Abstract

Dirhodium acetate catalyzed three-component reactions of aryl diazoacetates, alcohols or water, and 2-alkynals are reported to afford β-alkynyl α,β-dihydroxyl acid esters in good yield with high diastereoselectivity. Synthetic utility of the reaction was demonstrated in the conversion of the versatile alkynyl functionality to other synthetically useful compounds, including efficient synthesis of 2-aryl-2,3-dihydroxyl enelactones.

Graphical abstract: Diastereoselective three-component reactions of aryldiazoacetates with alcohols/water and alkynals: application to substituted enelactones

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Article information

DOI
https://doi.org/10.1039/C1OB05076A
Article type
Paper
Submitted
14 Jan 2011
Accepted
28 Feb 2011
First published
02 Mar 2011

Org. Biomol. Chem., 2011,9, 3839-3843

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Diastereoselective three-component reactions of aryldiazoacetates with alcohols/water and alkynals: application to substituted enelactones

X. Han, L. Jiang, M. Tang and W. Hu, Org. Biomol. Chem., 2011, 9, 3839 DOI: 10.1039/C1OB05076A

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