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Studies on the Reaction of Aryl Glyoxals with L-Prolinol: Unexpected Formation of Morpholin-2-one Derivatives and Stereoselective Trifluoromethylation of the Bicyclic System


Mloston, Grzegorz; Wroblewska, Aneta; Linden, Anthony; Heimgartner, Heinz (2015). Studies on the Reaction of Aryl Glyoxals with L-Prolinol: Unexpected Formation of Morpholin-2-one Derivatives and Stereoselective Trifluoromethylation of the Bicyclic System. Asian Journal of Organic Chemistry, 4:770-777.

Abstract

Reactions of L-prolinol with aryl glyoxals lead to labile bicyclic 2-aryloyl-1,3-oxazolidines, which smoothly undergo isomerization in the presence of an acid via a cascade of reactions involving a 1,2-aryl shift. The products formed thereby were identified as bicyclic derivatives of morpholin-2-one. Both 1,3-oxazolidines and morpholin-2-ones were used for the nucleophilic trifluoromethylation by treatment with trifluoromethyltrimethylsilane (Ruppert–Prakash reagent) in the presence of a catalytic amount of CsF. Whereas in the case of the 1,3-oxazolidines only modest diastereoselectivity was achieved, the reactions with the morpholinone derivatives occurred with complete stereoselectivity.

Abstract

Reactions of L-prolinol with aryl glyoxals lead to labile bicyclic 2-aryloyl-1,3-oxazolidines, which smoothly undergo isomerization in the presence of an acid via a cascade of reactions involving a 1,2-aryl shift. The products formed thereby were identified as bicyclic derivatives of morpholin-2-one. Both 1,3-oxazolidines and morpholin-2-ones were used for the nucleophilic trifluoromethylation by treatment with trifluoromethyltrimethylsilane (Ruppert–Prakash reagent) in the presence of a catalytic amount of CsF. Whereas in the case of the 1,3-oxazolidines only modest diastereoselectivity was achieved, the reactions with the morpholinone derivatives occurred with complete stereoselectivity.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:August 2015
Deposited On:12 Aug 2015 14:00
Last Modified:05 Apr 2016 19:21
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:2193-5807
Funders:National Science Center (Cracow, Poland)
Publisher DOI:https://doi.org/10.1002/ajoc.201500134

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