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Organocatalytic domino reaction of cyanosulfones: access to complex cyclohexane systems with quaternary carbon centers

Rajkumar, S., Shankland, K., Goodman, J. M. and Cobb, A. J.A. (2013) Organocatalytic domino reaction of cyanosulfones: access to complex cyclohexane systems with quaternary carbon centers. Organic Letters, 15 (6). pp. 1386-1389. ISSN 1523-7060

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To link to this item DOI: 10.1021/ol400356k

Abstract/Summary

When ε-nitro-a,β-unsaturated esters are added to conjugated cyanosulfones in the presence of a bifunctional thiourea catalyst, a highly stereoselective domino reaction occurs to generate complex cyclohexanes with up to four stereogenic centers, one of which is quaternary in nature. Therefore, it is demonstrated that, like nitro compounds, sulfones can undergo an asymmetric intramolecular conjugate addition to r,β- unsaturated esters in the presence of a bifunctional organocatalyst.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
ID Code:31384
Publisher:American Chemical Society

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