Abstract
Wender and Strand report the synthesis of 2,3-dihydropyrroles 3 via a formal [3+2] cycloaddition between aziridines 1 and unactivated acetylenes 2 under either Lewis or Brønsted acid catalysis. The silver-catalyzed process is tolerant of a wide range of substrates, including electron-rich and electron-poor acetylenes, and exhibits excellent levels of regioselectivity (>20:1 in favor of C2 R5 aryl products). The reaction is not limited to aryl acetylenes, with vinyl and alkyl groups also being tolerated, although Sc(OTf)3 was required as catalyst to effect the reaction of the latter substrate. Competition studies showed that electron-rich acetylenes undergo the reaction faster than electron-poor ones, indicating the capture of a cationic intermediate in the product-forming step.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
