Issue 9, 2018

NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

Abstract

The condensation reaction between a γ-methylene-α,β-unsaturated aldehyde and phenylpropargyl aldehyde was revisited and, guided by extensive DFT calculations of NMR shifts, was found to afford a deconjugative aldol condensation product. In this manner, a simple protocol for the preparation of valuable cross-conjugated oxatrienes was uncovered.

Graphical abstract: NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

Supplementary files

Article information

Article type
Communication
Submitted
15 Dec 2017
Accepted
24 Jan 2018
First published
24 Jan 2018

Org. Biomol. Chem., 2018,16, 1442-1447

NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

M. J. Riveira and A. M. Sarotti, Org. Biomol. Chem., 2018, 16, 1442 DOI: 10.1039/C7OB03110F

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