2024-03-29T01:30:06Z
https://niigata-u.repo.nii.ac.jp/oai
oai:niigata-u.repo.nii.ac.jp:00002610
2022-12-15T03:35:49Z
176:488:489
453:454
A facile synthetic method of α-quaternary-β,γ-unsaturated aldehydes via the stereoselective 1,4-elimination and α-regioselective Ferrier reaction
A facile synthetic method of α-quaternary-β,γ-unsaturated aldehydes via the stereoselective 1,4-elimination and α-regioselective Ferrier reaction
Tayama, Eiji
38101
Hashimoto, Ryo
38102
1,4-Elimination
1,3-Dienyl acetals
1-Alkoxy-1,3-dienes
Ferrier reaction
α-Quaternary-β,γ-unsaturated aldehydes
The 1,4-elimination reaction of 2-substituted-(2Z)-4-methoxy-O-alkenyl acetals with n-butyllithium is shown to afford the 2-substituted-(1Z,3E)-O-1,3-dienyl acetals in high stereoselectivities. The Ferrier reaction of the O-1,3-dienyl acetals thus obtained provides the corresponding α-quaternary-β,γ-unsaturated aldehydes in excellent yields with high α-regioselectivities.
journal article
Elsevier
2007-11
application/pdf
Tetrahedron letters
45
48
7950
7952
Tetrahedron letters
AA00861801
00404039
https://niigata-u.repo.nii.ac.jp/record/2610/files/1525A.pdf
eng
info:doi/10.1016/j.tetlet.2007.09.049