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Issue 39, 2019
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Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents

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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.

Graphical abstract: Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents

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Supplementary files

Article information


Submitted
27 Aug 2019
Accepted
12 Sep 2019
First published
16 Sep 2019

Org. Biomol. Chem., 2019,17, 8827-8831
Article type
Paper

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

Y. Wu and V. H. Rawal, Org. Biomol. Chem., 2019, 17, 8827
DOI: 10.1039/C9OB01880H

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