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Synfacts 2016; 12(09): 0925
DOI: 10.1055/s-0035-1562766
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric [4+1] Annulation of Sulfur Ylides

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Wang Q, Li T.-R, Lu L.-Q, * Li M.-M, Zhang K, Xiao W.-J. * Central China Normal University, Hubei and Lanzhou University, P. R. of China
Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper–Allenylidene Intermediates.

J. Am. Chem. Soc. 2016;
138: 8360-8363
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Publication History

Publication Date:
18 August 2016 (online)

 
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Key words

[4+1] annulation - sulfur ylides - copper catalysis - indolines

Significance

The authors report a copper-catalyzed asymmetric [4+1] cycloaddition by trapping copper–allenylidene dipolar intermediates with sulfur ylides. A variety of chiral indolines were obtained with high stereoselectivities (≤98% ee and dr > 95:5).


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Comment

This reaction affords an opportunity for the ready synthesis of chiral indoline products and related cycloadducts with high stereoselectivities. Mechanistic studies suggest that this reaction is a sequential process that involves decarboxylative propargylation/SN2 reactions promoted by binuclear copper complexes.


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