Gold‐ and Silver‐Catalyzed [4+2] Cycloadditions of Ynamides with Oxetanes and Azetidines. Issue 11 (17th July 2014)

• Record Type: Journal Article
• Authors: Pawar, Samir Kundlik; Vasu, Dhananjayan; Liu, Rai‐Shung
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 11/12(2014)
• Page Start: 2411
• Page End: 2416
• Publication Date: 2014-07-17
• 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.201400024
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Gold‐catalyzed [4+2] cycloadditions between ynamides and oxetanes are described; these reactions involve oxetanes and gold‐π‐ynamides as nucleophiles and electrophiles, respectively. Excellent cycloaddition regioselectivities are achieved over a reasonable range of ynamide and oxetane substrates. For azetidines, their [4+2] cycloadditions with ynamides are implemented more efficiently with silver hexafluoroantimonate, which is also compatible with various ynamides and azetidines. These two cycloadditions provide facile accesses to six‐membered heterocycles such as 6‐amino‐3, 4‐dihydro‐2<italic>H</italic>‐pyrans and 2‐amino‐1, 4, 5, 6‐tetrahydropyridines.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh11pkdphb" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>