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Chiral Anion Directed Asymmetric Carbocation-Catalyzed Diels-Alder Reactions
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 9, 1708-1713 p.Article in journal (Refereed) PublishedText
Abstract [en]

In recent years the carbocation has re-emerged as a highly efficient Lewis acid catalyst for a variety of organic transformations. However, the goal of asymmetric carbocation catalysis has so far been out of reach mainly as a result of difficulties associated with the preparation of stable chiral carbocations. Here, we describe developments towards asymmetric carbocation catalysis based on the concept of chiral-anion-directed catalysis. Chiral tritylium salts can be conveniently prepared in situ by mixing trityl chloride derivatives with chiral phosphonate, phosphoramide, bis(sulfonyl) amide, and bis(sulfuryl) amide silver or sodium salts. It is shown that the bis(sulfuryl) amide/tritylium ion salt catalyzes the Diels-Alder reaction with an up to 53 % enantiomeric excess.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2016. no 9, 1708-1713 p.
Keyword [en]
Synthetic methods, Asymmetric catalysis, Cycloaddition, Carbocations, Trityl ion
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-186566DOI: 10.1002/ejoc.201501621ISI: 000374149600012ScopusID: 2-s2.0-84959310716OAI: oai:DiVA.org:kth-186566DiVA: diva2:927996
Note

QC 20160513

Available from: 2016-05-13 Created: 2016-05-13 Last updated: 2016-05-13Bibliographically approved

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