Cycloaddition chemistry is an efficient strategy for the synthesis of diverse structural architectures. Donor-acceptor (DA) cyclobutanes have recently been reported to undergo efficient formal cycloadditions with a variety of dipolarophiles. We have most recently examined the reaction of alkoxy-activated DA cyclobutanes with nitrosoarenes under Lewis acid catalyzed conditions to form tetrahydro-1,2-oxazines. It was also observed that the electronics of the nitrosoarene and judicious selection of Lewis acid catalyst have a profound effect on the regio- and stereoselectivity of the reaction. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/nerm_2010/uploads/51373_qdbsa_uvvis.jpg' alt='' />

Formal [4+2] cycloaddition of alkoxy-substituted donor-acceptor cyclobutanes and nitrosoarenes

244th National Meeting (2012)

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