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Synthesis of N-BOC-3-azabicyclo[3.3.0]octan-7-one via reductive pauson-khand cyclization and subsequent conversion to a novel diazatricyclic ring system
Tetrahedron Letters
  • Daniel Becker, Loyola University Chicago
  • Daniel L. Flynn
Document Type
Article
Publication Date
6-4-1993
Pages
5047-5054
Publisher Name
Elsevier
Disciplines
Abstract

An intramolecular reductive Pauson-Khand reaction of the hexacarbonyldicobalt complex of N-(tert-butyloxycarbonyl)allylpropargylamine under dry-state adsorption conditions directly afforded the saturated N-BOC-3-azabicyclo[3.3.0]octan-7-one when the reaction was performed under an inert atmosphere. This bicyclic ketone was converted in several steps to the novel octahydro-1-azeto[2′,3′:3,4]cyclopenta[1,2-C]pyrrole ring system as confirmed by single crystal X-ray analysis.

Comments
Author Posting © Elsevier, 1993. This is the author's version of the work. It is posted here by permission of Elsevier for personal use, not for redistribution. The definitive version was published in Tetrahedron, Volume 49, Issue 23, June 4, 1993. http://dx.doi.org/10.1016/S0040-4020(01)81870-6
Creative Commons License
Creative Commons Attribution-Noncommercial-No Derivative Works 3.0
Citation Information
Daniel Becker and Daniel L. Flynn. "Synthesis of N-BOC-3-azabicyclo[3.3.0]octan-7-one via reductive pauson-khand cyclization and subsequent conversion to a novel diazatricyclic ring system" Tetrahedron Letters Vol. 49 Iss. 23 (1993)
Available at: http://works.bepress.com/daniel_p_becker/16/