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

✍ Scribed by Manoel T. Rodrigues Jr.; Juliana C. Gomes; Joel Smith; Fernando Coelho

• Book ID: 104098095
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 602 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.07.069

✦ Synopsis

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 N Ar 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.