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

Mitsuru Shindo, Soichiro Oya, Ryoko Murakami, Yusuke Sato, Kozo Shishido

Research output: Contribution to journal › Article

26 Citations (Scopus)

Abstract

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. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5947-5950
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number31
DOIs
Publication statusPublished - Jul 29 2000
Externally publishedYes

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Lactams
Lithium
Amides

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates. / Shindo, Mitsuru; Oya, Soichiro; Murakami, Ryoko; Sato, Yusuke; Shishido, Kozo.

In: Tetrahedron Letters, Vol. 41, No. 31, 29.07.2000, p. 5947-5950.

Research output: Contribution to journal › Article

Shindo, M, Oya, S, Murakami, R, Sato, Y & Shishido, K 2000, 'Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates', Tetrahedron Letters, vol. 41, no. 31, pp. 5947-5950. https://doi.org/10.1016/S0040-4039(00)00986-2
Shindo M, Oya S, Murakami R, Sato Y, Shishido K. Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates. Tetrahedron Letters. 2000 Jul 29;41(31):5947-5950. https://doi.org/10.1016/S0040-4039(00)00986-2
Shindo, Mitsuru ; Oya, Soichiro ; Murakami, Ryoko ; Sato, Yusuke ; Shishido, Kozo. / Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 31. pp. 5947-5950.
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