NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α, β-unsaturated aldehydes and propargyl aldehydes. Issue 9 (8th February 2018)

• Record Type: Journal Article
• Authors: Riveira, Martín J.; Sarotti, Ariel M.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 9(2018)
• Page Start: 1442
• Page End: 1447
• Publication Date: 2018-02-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob03110f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An experimental and computational study of the reaction between γ-methylene enals and propargyl aldehydes uncovered a deconjugative aldol condensation. 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.