New method for activation of aldimines in cycloaddition of lithium ynolates with N-2-methoxyphenyl imines leading to β-lactams

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

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The cycloaddition of the N-2-methoxyphenyl aldimines with lithium ynolates was efficiently accelerated via chelation to give β-lactam enolates, which immediately reacted with one more equivalent of the imine to give β-lactams (2:1 adducts) in good yields, while N-4-methoxyphenyl imines were inert towards lithium ynolates. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5943-5946
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number31
DOIs
Publication statusPublished - Jul 29 2000
Externally publishedYes

Fingerprint

Lactams
Imines
Cycloaddition
Cycloaddition Reaction
Lithium
Chemical activation
Chelation

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

New method for activation of aldimines in cycloaddition of lithium ynolates with N-2-methoxyphenyl imines leading to β-lactams. / Shindo, Mitsuru; Oya, Soichiro; Murakami, Ryoko; Sato, Yusuke; Shishido, Kozo.

In: Tetrahedron Letters, Vol. 41, No. 31, 29.07.2000, p. 5943-5946.

Research output: Contribution to journalArticle

Shindo, Mitsuru ; Oya, Soichiro ; Murakami, Ryoko ; Sato, Yusuke ; Shishido, Kozo. / New method for activation of aldimines in cycloaddition of lithium ynolates with N-2-methoxyphenyl imines leading to β-lactams. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 31. pp. 5943-5946.
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