Diastereoselective Indole-Dearomative Cope Rearrangements by Compounding Minor Driving Forces

Subhadip De, Breanna M. Tomiczek, Yinuo Yang, Kenneth Ko, Ion Ghiviriga, Adrian Roitberg, Alexander J. Grenning

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Reported herein is the discovery of a diastereoselective indole-dearomative Cope rearrangement. A suite of minor driving forces promote dearomatization: (i) steric congestion in the starting material, (ii) alkylidene malononitrile and stilbene conjugation events in the product, and (iii) an unexpected intramolecular π-π∗ stack on the product side of the equilibrium. The key substrates are rapidly assembled from simple starting materials, resulting in many successful examples. The products are structurally complex and bear vicinal stereocenters generated by the dearomative Cope rearrangement. They also contain a variety of functional groups for interconversion to complex architectures.

Original languageEnglish (US)
Pages (from-to)3726-3730
Number of pages5
JournalOrganic Letters
Volume24
Issue number20
DOIs
StatePublished - May 27 2022
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2022 The Authors. Published by American Chemical Society.

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