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Synfacts 2013; 9(1): 0056
DOI: 10.1055/s-0032-1317777
DOI: 10.1055/s-0032-1317777
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Copper-Catalyzed Enantioselective Incorporation of Ketones to Hemiaminals
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
17. Dezember 2012 (online)

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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