Diastereoselective Intramolecular Cyanoamidation with Alkenes

Ashley M. Dreis, Sadie C. Otte, Matthew S. Eastwood, Elizabeth R. Alonzi, Jason T. Brethorst, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.

Original languageEnglish (US)
Pages (from-to)45-48
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number1
DOIs
StatePublished - Jan 3 2017

Bibliographical note

Funding Information:
This work was funded by the National Institute of Health (R01 GM095559). NMR spectra were recorded on an instrument purchased with support from the National Institute of Health (S10 OD011952). E. R. A. thanks the University of Minnesota for support through the Undergraduate Research Opportunities Program (UROP) award. We also thank Dr. Letitia Yao (UMN) for NMR assistance and Zhongda Pan (UMN) for constructive conversations and purification of chemical reagents.

Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Bond Activation
  • Cyanoamidation
  • Diastereoselectivity
  • Homogeneous catalysis
  • Palladium

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