Research Article

Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar Cycloaddition of 2-Acyl-5-aminooxazolium Salts

Published: 2012-11-16

Journal: The Journal of Organic Chemistry

DOI: 10.1021/jo301600p

Abstract

### Abstract A concise method for the diastereoselective synthesis of octahydroindoles is presented. The products contain 2-amido and 7-hydroxyl substituents. A series of 2-acyl-5-aminooxazoles were prepared in one step. Upon methylation of the oxazole nitrogen atom, the substrates underwent rapid intramolecular 1,3-dipolar cycloaddition with a tethered alkene and, after reduction with excess hydride, produced octahydroindoles with excellent diastereoselectivity. The method allows for the installation of α-quaternary stereogenic carbon atoms. ### Keywords 1,3-Dipolar Cycloaddition, Octahydroindoles, Diastereoselectivity, Synthesis ### Authors - Corey H. Basch† - Jameson A. Brinck† - Joaquin E. Ramos† - Stephen A. Habay*† - Glenn P.A. Yap‡ ### Correspondence *Stephen A. Habay, Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, United States; Email: sahabay@salisbury.edu ### Publication Information - **Journal:** The Journal of Organic Chemistry - **Volume:** 77 - **Issue:** 22 - **Pages:** 10416-10421 - **Published:** October 23, 2012 - **Received:** August 1, 2012 - **Published Online:** October 26, 2012 - **Published in Issue:** November 16, 2012 ### Acknowledgments High-resolution mass spectrometry analysis support from Jay Khalin and Dr. John Greaves and HPLC–MS assistance from Dr. Stephen Chan is gratefully acknowledged. This research was supported by awards from Research Corporation for Science Advancement and Salisbury University.

Faculty Members

  • Stephen A. Habay - Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, United States
  • Jameson A. Brinck - Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, United States
  • Corey H. Basch - Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, United States
  • Joaquin E. Ramos - Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, United States
  • Glenn P.A. Yap - Department of Chemistry & Biochemistry, University of Delaware, 236 Brown Laboratory, Newark, Delaware 19716, United States

Themes

  • Octahydroindoles
  • Diastereoselective synthesis
  • Chemical modifications
  • Synthesis of complex organic molecules

Categories

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