One-Pot Synthesis of Chiral Tetracyclic Dibenzo[ b, f][1,4]oxazepine-Fused 1,2-Dihydropyridines (DHPs) under Metal-Free Conditions

Abstract

An efficient protocol for the catalytic asymmetric synthesis of new dibenzo[b,f][1,4]-oxazepine-fused 1,2-dihydropyridines (DHPs) has been described under metal-free conditions. This reaction proceeds through proline-catalyzed direct Mannich/cyclization between seven-membered dibenzo[b,f][1,4]-oxazepine-imines and aqueous glutaraldehyde, followed by IBX-mediated site-selective dehydrogenative oxidation in one-pot operation with high yields (up to 92%) and excellent enantioselectivity (up to >99:1 er).