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Synfacts 2013; 9(1): 0061
DOI: 10.1055/s-0032-1317751
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition

Contributor(s):
Mark Lautens
,
Lei Zhang
Trost BM, * Morris PJ, Sprague SJ. Stanford University, USA
Palladium-Catalyzed Diastereo- and Enantioselective Formal [3 + 2]-Cycloadditions of Substituted Vinylcyclopropanes.

J. Am. Chem. Soc. 2012;
134: 17823-17831
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

palladium - Trost ligand - vinylcyclopropanes - formal [3+2] cycloaddition - cyclopentanes

Significance

A palladium-catalyzed asymmetric formal [3+2] cycloaddition of vinylcyclopropanes to electron-poor olefins is reported using the Trost ligand. The developed method can access highly substituted cyclopentanes with high diastereo- and enantioselectivity with moderate to high yield.


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Comment

As the vinylcyclopropanes 1 used are racemic, the authors propose that the reaction occurs under Curtin–Hammett conditions for this stereo-convergent reaction. Notably, the effects of π–σ– π interconversion and the reversibility of the conjugate addition establish pre-equilibria of diastereomeric reactive intermediates 4 and 5, consequently favoring the formation of 3.


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