A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence
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DW TFJ Org Lett 2 2012.pdf
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Author(s)
Webb, Damien
Jamison, Timothy F.
Date Issued
April 2012
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Webb, Damien, and Timothy F. Jamison. “A Continuous Homologation of Esters: An Efficient Telescoped Reduction–Olefination Sequence.” Organic Letters 14.10 (2012): 2465–2467.
Version
Author's final manuscript
Abstract
A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner–Wadsworth–Emmons olefination, thus converting a three-operation procedure into a single, uninterrupted system that eliminates the need for isolation or purification of the aldehyde intermediates. The homologated products are obtained in high yield and selectivity.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ol300722e
