Simple and highly diastereoselective access to 3,4-substituted tetrahydro-1,8-naphthyridines from Morita-Baylis-Hillman adducts

We disclose herein a facile and straightforward method to access 3,4-substituted tetrahydro-1,8-naphthyridines from Morita-Baylis-Hillman. The strategy is based on a tandem sequence involving a Michael addition reaction followed by an intramolecular S_NAr reaction on a silylated-Morita-Baylis-Hillman adduct. In a single step, a new cycle is formed and the relative stereochemistry of two new centers is controlled with good to excellent diastereoselectivity.