Chiral Lewis acid-catalyzed enantioselective intramolecular carbonyl ene reactions of unsaturated alpha-keto esters

Dan Yang; Min Yang; Nian-Yong Zhu

doi:10.1021/ol035486d

Chiral Lewis acid-catalyzed enantioselective intramolecular carbonyl ene reactions of unsaturated alpha-keto esters

Org Lett. 2003 Oct 2;5(20):3749-52. doi: 10.1021/ol035486d.

Authors

Dan Yang¹, Min Yang, Nian-Yong Zhu

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China. [email protected]

PMID: 14507221
DOI: 10.1021/ol035486d

Abstract

[reaction: see text] Chiral Lewis acid-promoted highly enantioselective intramolecular carbonyl ene reactions of unsaturated alpha-keto esters have been investigated. In the presence of chiral Lewis acids such as [Sc((R,R)-Ph-pybox)](OTf)(3) and [Cu((S,S)-Ph-box)](OTf)(2), several unsaturated alpha-keto esters underwent carbonyl ene reactions in CH(2)Cl(2) at room temperature to give monocyclic products in good yield and excellent enantioselectivity.