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Selected Works

Daniel P. Becker

2016

Articles 1 - 2 of 2

Full-Text Articles in Physical Sciences and Mathematics

Studies Of The Solid-Phase Pauson-Khand Reaction Selective In-Situ Enone Reduction To 3-Azabicyclo[3.3.0]Oct-Anones, Daniel Becker, Daniel L. Flynn Feb 2016

Studies Of The Solid-Phase Pauson-Khand Reaction Selective In-Situ Enone Reduction To 3-Azabicyclo[3.3.0]Oct-Anones, Daniel Becker, Daniel L. Flynn

Daniel P. Becker

The Smit-Caple DSAC Pauson-Khand cyclization of a series of N-protected allyl propargyl amines in the absence of oxygen gave rise to formation of the saturated azabicyclo[3.3.0]octanones in excellent yields. Standard cyclization in air gave mixtures of saturated and unsaturated ketones.


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, Daniel Becker, Daniel L. Flynn Feb 2016

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, Daniel Becker, Daniel L. Flynn

Daniel P. Becker

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.