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Synfacts 2013; 9(1): 0056
DOI: 10.1055/s-0032-1317777
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Enantioselective Incorporation of Ketones to Hemiaminals

Contributor(s):
Hisashi Yamamoto
,
Susumu Oda
Shi SL, Wei XF, Shimizu Y, Kanai M * The University of Tokyo and Japan Science and Technology Agency, Kawaguchi-shi, Japan
Copper(I)-Catalyzed Enantioselective Incorporation of Ketones to Cyclic Hemiaminals for the Synthesis of Versatile Alkaloid Precursors.

J. Am. Chem. Soc. 2012;
134: 17019-17022
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

copper - ketones - hemiaminals

Significance

The authors developed a copper-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals. A series of hemiaminals, including five-, six- and seven-membered rings, were applicable to provide versatile alkaloid precursors in high yield with excellent enantioselectivity.


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Comment

This reaction proceeds through three successive steps: aldol reaction, dehydration and intramolecular enantioselective aza-Michael reaction. Employment of this pathway contributed to improve the reaction conditions and expand the substrate scope. Synthetic utility was demonstrated by the preparation of alkaloid and drug precursors.


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