Cycloaddition of lithium ynolate to imines: Synthesis of 3,4-disubstituted β-lactams

Mitsuru Shindo, Soichiro Oya, Yusuke Sato, Kozo Shishido

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Cycloaddition reaction of a lithium ynolate to N-sulfonylimines afforded 3,4-disubstituted β-lactams. The cis-products were synthesized in high diastereoselectivity via quenching of the intermediate, β-lactam enolates, with phenol.

Original languageEnglish
Pages (from-to)113-116
Number of pages4
JournalHeterocycles
Volume49
Issue number1
DOIs
Publication statusPublished - Dec 31 1998
Externally publishedYes

Fingerprint

Lactams
Imines
Cycloaddition
Cycloaddition Reaction
Lithium
Phenol
Quenching
N-sulfonylimine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Cycloaddition of lithium ynolate to imines : Synthesis of 3,4-disubstituted β-lactams. / Shindo, Mitsuru; Oya, Soichiro; Sato, Yusuke; Shishido, Kozo.

In: Heterocycles, Vol. 49, No. 1, 31.12.1998, p. 113-116.

Research output: Contribution to journalArticle

Shindo, Mitsuru ; Oya, Soichiro ; Sato, Yusuke ; Shishido, Kozo. / Cycloaddition of lithium ynolate to imines : Synthesis of 3,4-disubstituted β-lactams. In: Heterocycles. 1998 ; Vol. 49, No. 1. pp. 113-116.
@article{75f5b4b0cd82495788cea3e68f83d164,
title = "Cycloaddition of lithium ynolate to imines: Synthesis of 3,4-disubstituted β-lactams",
abstract = "Cycloaddition reaction of a lithium ynolate to N-sulfonylimines afforded 3,4-disubstituted β-lactams. The cis-products were synthesized in high diastereoselectivity via quenching of the intermediate, β-lactam enolates, with phenol.",
author = "Mitsuru Shindo and Soichiro Oya and Yusuke Sato and Kozo Shishido",
year = "1998",
month = "12",
day = "31",
doi = "10.3987/COM-98-S52",
language = "English",
volume = "49",
pages = "113--116",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "1",

}

TY - JOUR

T1 - Cycloaddition of lithium ynolate to imines

T2 - Synthesis of 3,4-disubstituted β-lactams

AU - Shindo, Mitsuru

AU - Oya, Soichiro

AU - Sato, Yusuke

AU - Shishido, Kozo

PY - 1998/12/31

Y1 - 1998/12/31

N2 - Cycloaddition reaction of a lithium ynolate to N-sulfonylimines afforded 3,4-disubstituted β-lactams. The cis-products were synthesized in high diastereoselectivity via quenching of the intermediate, β-lactam enolates, with phenol.

AB - Cycloaddition reaction of a lithium ynolate to N-sulfonylimines afforded 3,4-disubstituted β-lactams. The cis-products were synthesized in high diastereoselectivity via quenching of the intermediate, β-lactam enolates, with phenol.

UR - http://www.scopus.com/inward/record.url?scp=0032585427&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032585427&partnerID=8YFLogxK

U2 - 10.3987/COM-98-S52

DO - 10.3987/COM-98-S52

M3 - Article

AN - SCOPUS:0032585427

VL - 49

SP - 113

EP - 116

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 1

ER -