relation: http://d-scholarship-dev.library.pitt.edu/9096/
title: The Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters to Prepare α-Acetoxy 4-Alkylidene Cyclopent-3-en-2-ones
creator: Davis, Matthew M
description: The Rh(I)-catalyzed allenic cyclocarbonylation reaction is an effective method for forming 4-alkylidene cyclopentenones. The scope of this methodology was expanded to include the cyclocarbonylation of allenol acetates to provide α-acetoxy-4-alkylidene cyclopentenones. The diastereoselectivity of the [3,3]-sigmatropic rearrangement to form the allenol acetates and cyclocarbonylation reaction were examined. During the course of the Rh(I)-catalyzed cyclocarbonylation reaction two rhodium metallocycle intermediates were observed and structures are postulated based upon 1H and 13C NMR data. Liberation of the acetate to the free alcohol was also accomplished yielding α-hydroxy-4-alkylidene cyclopentenones.
date: 2009-09-29
type: University of Pittsburgh ETD
type: PeerReviewed
format: application/pdf
language: en
identifier: http://d-scholarship-dev.library.pitt.edu/9096/1/Masters_Thesis_Matthew_M_Davis_8_18_2009.pdf
identifier:   Davis, Matthew M  (2009) The Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters to Prepare α-Acetoxy 4-Alkylidene Cyclopent-3-en-2-ones.  Master's Thesis, University of Pittsburgh.    (Unpublished)