A Homo [3+2] Dipolar Cycloaddition: The Reaction of Nitrones with Cyclopropanes

Abstract

Pole-to-pole: Cyclopropanediesters when treated with nitrones in the presence of catalytic ytterbium triflate undergo a dipolar homo [3+2] cycloaddition to form tetrahydro-1,2-oxazines diastereoselectively (see scheme). This new process has been used in a two-step preparation of the tricyclic core of FR-900482. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z51573_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.