Studies on the Reaction of Aryl Glyoxals with l‐Prolinol: Unexpected Formation of Morpholin‐2‐one Derivatives and Stereoselective Trifluoromethylation of the Bicyclic System. Issue 8 (12th June 2015)

• Record Type: Journal Article
• Authors: Mlostoń, Grzegorz; Wróblewska, Aneta; Linden, Anthony; Heimgartner, Heinz
• Is Part Of: Asian journal of organic chemistry. Volume 4:Issue 8(2015:Aug.)
• Page Start: 770
• Page End: 777
• Publication Date: 2015-06-12
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201500134
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Reactions of <sc>l</sc>‐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.</p> </abstract>