The Enantioselective, Organocatalyzed Diels–Alder Reaction of 2-Vinylindoles with ,β-Unsaturated Aldehydes: An Efficient Route to Functionalized Tetrahydrocarbazoles

摘要

Prolinol catalysts: A highly enantio- and diastereoselective prolinol-catalyzed Diels–Alder reaction of 2-vinylindoles and ,β-unsaturated aldehydes is developed (see scheme). This methodology allows the development of further applications of prolinols in asymmetric synthesis. The resulting densely functionalized enantiomerically pure tetrahydrocarbazoles are useful in the total synthesis of natural products such as the core structure of the akuammiline alkaloid vincorine.