The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Author:

Hu Miao1ORCID,Ding Hao1ORCID,DeSnoo William2ORCID,Tantillo Dean J.2ORCID,Nairoukh Zackaria1ORCID

Affiliation:

1. Institute of Chemistry The Hebrew University of Jerusalem Jerusalem 9190401 Israel

2. Department of Chemistry University of California-Davis Davis CA 95616 USA

Abstract

AbstractNitrogen heterocycles play a vital role in pharmaceuticals and natural products, with the six‐membered aromatic and aliphatic architectures being commonly used. While synthetic methods for aromatic N‐heterocycles are well‐established, the synthesis of their aliphatic functionalized analogues, particularly piperidine derivatives, poses a significant challenge. In that regard, we propose a stepwise dearomative functionalization reaction for the construction of highly decorated piperidine derivatives with diverse functional handles. We also discuss challenges related to site‐selectivity, regio‐ and diastereoselectivity, and provide insights into the reaction mechanism through mechanistic studies and density functional theory computations.

Publisher

Wiley

Subject

General Medicine

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