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One-Step Catalytic Enantioselective a-Quaternary 5-Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized a-Quaternary Proline Derivatives
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2012 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 6, 1156-1162 p.Article in journal (Refereed) Published
Abstract [en]

The highly enantioselective cascade reaction between N-protected a-cyanoglycine esters and a,beta-unsaturated aldehydes is disclosed. The reaction represents a one-step entry to polysubstituted 5-hydroxyproline derivatives having a quaternary a-stereocenter generally in high yields with up to >95:5 dr and 99:1 er. It is also a direct catalytic two-step entry to functionalized a-quaternary proline derivatives.

Place, publisher, year, edition, pages
2012. Vol. 354, no 6, 1156-1162 p.
Keyword [en]
asymmetric catalysis, hemiaminals, metal-free catalysis, proline derivatives, quaternary stereocenters, tandem reactions
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-80736DOI: 10.1002/adsc.201100911ISI: 000302936000025OAI: oai:DiVA.org:su-80736DiVA: diva2:558650
Funder
Swedish Research Council
Note

AuthorCount:7;

Available from: 2012-10-04 Created: 2012-09-27 Last updated: 2017-12-07Bibliographically approved

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Deiana, LucaSun, JunliangCordova, Armando
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