Proline Sulfonamide-Catalyzed, ­Domino Process for Asymmetric Synthesis of Amino- and Hydroxy-Substituted Bicyclo[2.2.2]octanes

Authors

El-Mansy Mohamed, Oregon State University
Jun Y. Kang, University of Nevada, Las VegasFollow
Rajinikanth Lingampally, Oregon State University
Rich G. Carter, Oregon State UniversityFollow

Document Type

Article

Publication Date

11-25-2015

Publication Title

European Journal of Organic Chemistry

Volume

2016

Issue

1

First page number:

150

Last page number:

157

Abstract

A generalized method for accessing highly functionalized amino-substituted bicyclo[2.2.2]octanes via p-dodecylphenylsulfonamide catalyst in a good enantio- and diastereoselective fashion has been developed. A discussion of the mechanistic underpinnings of this transformation is presented. Finally, an unexpected discovery enabling the extension of this protocol to the synthesis of OH-substituted bicyclo[2.2.2]octanes with encouraging levels of stereoselectivity is discussed.

File Format

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File Size

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Repository Citation

Mohamed, E., Kang, J. Y., Lingampally, R., Carter, R. G. (2015). Proline Sulfonamide-Catalyzed, ­Domino Process for Asymmetric Synthesis of Amino- and Hydroxy-Substituted Bicyclo[2.2.2]octanes. European Journal of Organic Chemistry, 2016(1), 150-157.
http://dx.doi.org/10.1002/ejoc.201501302