Selective Reduction of α,β-Unsaturated Weinreb Amides in the Presence of α,β-Unsaturated Esters

Kenta Morita; Kenichi Murai; Mitsuhiro Arisawa; Hiromichi Fujioka

doi:10.1248/cpb.c20-00545

Notes

Selective Reduction of α,β-Unsaturated Weinreb Amides in the Presence of α,β-Unsaturated Esters

Kenta Morita, Kenichi Murai, Mitsuhiro Arisawa, Hiromichi Fujioka

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Keywords: chemoselective, in situ protection, reduction, α,β-unsaturated Weinreb amide, α,β-unsaturated ester

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2020 Volume 68 Issue 11 Pages 1100-1103

DOI https://doi.org/10.1248/cpb.c20-00545

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Abstract

α,β-Unsaturated esters were selectively protected in situ in the presence of α,β-unsaturated Weinreb amides using PEt₃ and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in toluene under reflux. Diisobutylaluminium hydride (DIBAL-H) reduction of the mixture followed by tetra-n-butylammonium fluoride (TBAF) treatment produced α,β-unsaturated aldehydes in good yields along with the recovered α,β-unsaturated esters.

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