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Synfacts 2013; 9(5): 0505
DOI: 10.1055/s-0033-1338383
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Synthesis of Piperidines by a [6+3] Cycloaddition

Contributor(s):
Mark Lautens
,
Harald Weinstabl
He Z.-L, Teng H.-L, Wang C.-J * Wuhan University and Nankai University, Tianjin, P. R. of China
Fulvenes as Effective Dipolarophiles in Copper(I)-Catalyzed [6+3] Cycloaddition of Azomethine Ylides: Asymmetric Construction of Piperidine Derivatives.

Angew. Chem. Int. Ed. 2013;
52: 2934-2938
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Publication History

Publication Date:
17 April 2013 (online)

 
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Key words

azomethine ylides - copper - cycloaddition - heterocycles

Significance

Hong et al. (Org. Lett. 2003, 5, 1689) reported a [6+3] cycloaddition of azomethine ylides with fulvenes, thus leading to the synthesis of racemic six-membered piperidine derivatives. However, there is a lack of catalytic asymmetric variants with high functional group tolerability.


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Comment

A highly efficient asymmetric copper(I)–TF-BiphamPhos-catalyzed [6+3] cycloaddition was developed, which shows very good yields, high regioselectivity and excellent enantio­selectivity. Due to its high functional group tolerance, the products can be easily modified.


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