A Two-Step, Formal [4 + 2] Approach toward Piperidin-4-ones via Au Catalysis

摘要

The piperidine ring is an essential building block in many bioactive alkaloids, and modular constructions of functionalized piperidines such as piperidin-4-ones can serve as powerful tools in alkaloid synthesis.rnIn our ongoing program of expanding gold catalysis into N-heterocycle synthesis, we have developed an efficient, two-step synthesis of piperidin-4-ones in a formal [4 + 2] manner from secondary amines. Herein, we disclose the details of this chemistry, including its regioselectivity and diastereoselectivity as well as its application in a highly diastereoselective synthesis of (±)-cermizine C.