Highly E-selective synthesis of α,β-unsaturated amides from N-2-methoxyphenyl aldimines via lithium ynolates

Lithium ynolates reacted with N-2 -methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro-Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates.

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Bibliographic Details
Published in:Tetrahedron letters 2000-07, Vol.41 (31), p.5947-5950
Main Authors: Shindo, Mitsuru, Oya, Soichiro, Murakami, Ryoko, Sato, Yusuke, Shishido, Kozo
Format: Article
Language:English
Subjects:
amides
imines
olefination
ynolates
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Description
Summary:Lithium ynolates reacted with N-2 -methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro-Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00986-2