Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

Barry M. Trost, Christopher A. Kalnmals, Divya Ramakrishnan, Michael C. Ryan, Rebecca W. Smaha, Sean Parkin

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.

Original languageEnglish
Pages (from-to)2584-2589
Number of pages6
JournalOrganic Letters
Volume22
Issue number7
DOIs
StatePublished - Apr 3 2020

Bibliographical note

Funding Information:
We thank the Tamaki Foundation and Chugai Pharmaceuticals for their generous partial financial support of our program. Part of this work was performed at the Stanford Nano Shared Facilities (SNSF), supported by the National Science Foundation under Award ECCS-1542152. D.R. thanks Stanford Chemistry for two Undergraduate Summer Research Fellowships. We also thank Dr. Elumalai Gnanamani (Stanford University) and Dr. Jana Maclaren (Stanford University) for assistance in obtaining a crystal structure of 9mj .

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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