The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Miao Hu, Hao Ding, William DeSnoo, Dean J. Tantillo*, Zackaria Nairoukh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Nitrogen 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.

Original languageAmerican English
Article numbere202315108
JournalAngewandte Chemie - International Edition
Volume62
Issue number49
DOIs
StatePublished - 4 Dec 2023

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Keywords

  • Carbopalladation
  • Dearomative Functionalization
  • Functional Molecules
  • Heterocycles
  • Stereoselectivity

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