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Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes
2005 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 45, 15710-15711 p.Article in journal (Refereed) Published
Abstract [en]

An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the β-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the α-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino−thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to α,β-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2005. Vol. 127, no 45, 15710-15711 p.
Keyword [en]
carbonyl-compounds, michael addition, cyclic enones, catalyst, organocatalysis, ether
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-15200DOI: 10.1021/ja055291wISI: 000233535400025Scopus ID: 2-s2.0-27844440320OAI: oai:DiVA.org:kth-15200DiVA: diva2:333241
Note

QC 20100525

Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved

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Franzen, Johan.

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