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. 2013 Apr 4;49(26):2616-8.
doi: 10.1039/c3cc40634b.

Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes

Casi M Schienebeck  1 , Patrick J Robichaux, Xiaoxun Li, Lianqing Chen, Weiping Tang
Affiliations

Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes

Casi M Schienebeck et al. Chem Commun (Camb). .

Abstract

We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most terminal alkynes.

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Figures

Scheme 1
Scheme 1
Five-Carbon Building Blocks for Rh-Catalyzed [5 + 2] Cycloadditions
Scheme 2
Scheme 2
Proposed Mechanism for Rh-Catalyzed Intermolecular [5 + 2] Cycloaddition of ACE and Alkyne
See this image and copyright information in PMC

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