Issue 1, 2011
From the journal:

Organic & Biomolecular Chemistry

Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts†

Thomas C. Nugent,*a   Mohammad Shoaiba  and  Amna Shoaiba  

* Corresponding authors

a Department of Chemistry, School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, Germany
E-mail: t.nugent@jacobs-university.de
Fax: +49 421 200 3229
Tel: +49 421 200 3232

Abstract

A three component catalyst system entailing an amino acid (OtBu-L-threonine), a hydrogen bond donor (sulfamide), and an amine base (DMAP) allows α-branched aldehyde addition to nitroalkenes in good to high yield and excellent ee. Importantly, the lowest reported catalyst loading (5.0 mol%) and aldehyde stoichiometry (1.2–2.0 equiv) is demonstrated and in most instances the best current product profile is observed.

Graphical abstract: Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts

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Article information

DOI
https://doi.org/10.1039/C0OB00822B
Article type
Communication
Submitted
04 Oct 2010
Accepted
06 Oct 2010
First published
21 Oct 2010

Org. Biomol. Chem., 2011,9, 52-56

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Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts

T. C. Nugent, M. Shoaib and A. Shoaib, Org. Biomol. Chem., 2011, 9, 52 DOI: 10.1039/C0OB00822B

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