Rapid construction of tetrahydropyridine scaffolds via formal imino Diels-Alder reactions of Schiff bases and Nazarov reagents

Yen-Ku Wu, Viresh H. Rawal

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Described is a one-flask, two-step method for the synthesis of highly functionalized piperidines. The process involves formal [4 + 2] cycloadditions of Schiff bases and Nazarov reagents, followed by facile elaborations of the initial cycloadducts. Notably, these aza-annulations are facilitated by protic solvents and proceed smoothly under ambient conditions, without other additives. The synthetic utility of this annulation protocol is further showcased through a concise, convergent synthesis of (±)-tetrabenazine.

Original languageEnglish
Pages (from-to)8827-8831
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number39
DOIs
StatePublished - 21 Oct 2019

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