Photochemical transformations have been demonstrated extensively in natural product synthesis, and are particularly advantageous when mild and efficient C�C and C�O bond formations are employed. Utilizing [2 + 2] cycloaddition reactions to prepare cyclobutane derivatives, up to four carbon stereocenters can be generated in one synthetic step.  Recent reports have outlined progress in the development of enantioselective photochemical reactions through intermolecular host-guest pairing in solution through hydrogen bonding with a rigid, chiral host.  In order to expand upon this methodology, substituted oxazinone (1  ) and related uracil photosubstrates are prepared through microwave irradiation.  Both intra- and intermolecular photocycloadditions of these substrates are investigated with a known H-bonding host as well as with thiourea and thioamide based H-bonding hosts similar to 2 .

Asymmetric host-guest [2 + 2] photocycloadditions with thioamide and thiourea hydrogen-bonding hosts

244th National Meeting (2012)

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