An Aminopyridinato Titanium Catalyst for the Intramolecular Hydroaminoalkylation of Secondary Aminoalkenes. Issue 10 (6th July 2015)

• Record Type: Journal Article
• Authors: Dörfler, Jaika; Bytyqi, Besnik; Hüller, Sascha; Mann, Nicola M.; Brahms, Christian; Schmidtmann, Marc; Doye, Sven
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 10(2015)
• Page Start: 2265
• Page End: 2276
• Publication Date: 2015-07-06
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500287
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The easily accessible 2‐(methylamino)pyridinato titanium complex initially synthesized by Kempe is used as catalyst for efficient intramolecular hydroaminoalkylation reactions of secondary aminoalkenes. The corresponding reactions of <italic>N</italic>‐aryl‐substituted 1‐aminohept‐6‐enes and 1‐aminohex‐5‐enes directly give access to 2‐methylcyclohexyl‐ or 2‐methylcyclopentylamines in good yields. In addition, intramolecular hydroaminoalkylations of an <italic>N</italic>‐alkyl‐substituted secondary aminoalkene and a geminally β‐disubstituted substrate are described for the first time. While all products are formed as mixtures of two diastereoisomers, better <italic>trans</italic>/<italic>cis</italic> ratios are observed during the formation of 2‐methylcylopentylamines.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj22cj58j5" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>