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Synthesis 2018; 50(22): 4476-4482
DOI: 10.1055/s-0036-1591597
DOI: 10.1055/s-0036-1591597
paper
Synthesis of (Z)-2-[(tert-Butyldimethylsilyl)oxy]-3-(phenylthio) acrylaldehyde
This work was supported by the National Science Foundation (CHE-1463724).Further Information
Publication History
Received: 28 April 2018
Accepted after revision: 05 June 2018
Publication Date:
17 July 2018 (online)
Dedicated to Professor Scott E. Denmark on the occasion of his 65th birthday.
Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.
Abstract
The title compound was prepared from ethyl acrylate over seven steps. En route, an ester was prepared that could be catalytically activated with Sc(OTf)3 to undergo a (4+3) cycloaddition with 2,5-dimethylfuran. The title compound reacts with organolithium species and the resultant alkoxide can be trapped as an ester or allowed to experience a silyl shift to produce a highly functionalized ketone.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591597.
- Supporting Information
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