Generation and reaction of copper(I) hydride in the copper(I) chloride-tributyltin hydride-NMP system

Synthesis of 3-norcephalosporin

Hideo Tanaka, Yoshihiko Yamaguchi, Shin Ichi Sumida, Manabu Kuroboshi, Misato Mochizuki, Sigeru Torii

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of either 3-trifluoromethylsulfonyloxy-Δ3-cephem 2, allenecarboxylate 3 or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributyltin hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a copper(I) hydride species in the copper(I) chloride-tributyltin hydride-NMP or N,N-dimethylformamide (DMF) system are discussed.

Original languageEnglish
Pages (from-to)3463-3468
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number23
Publication statusPublished - Dec 7 1999

Fingerprint

Hydrides
Copper
Dimethylformamide
tributyltin
cuprous chloride

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

Cite this

Generation and reaction of copper(I) hydride in the copper(I) chloride-tributyltin hydride-NMP system : Synthesis of 3-norcephalosporin. / Tanaka, Hideo; Yamaguchi, Yoshihiko; Sumida, Shin Ichi; Kuroboshi, Manabu; Mochizuki, Misato; Torii, Sigeru.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 23, 07.12.1999, p. 3463-3468.

Research output: Contribution to journalArticle

@article{579b7bc8aae54104960f99b1f8e48731,
title = "Generation and reaction of copper(I) hydride in the copper(I) chloride-tributyltin hydride-NMP system: Synthesis of 3-norcephalosporin",
abstract = "Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of either 3-trifluoromethylsulfonyloxy-Δ3-cephem 2, allenecarboxylate 3 or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributyltin hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a copper(I) hydride species in the copper(I) chloride-tributyltin hydride-NMP or N,N-dimethylformamide (DMF) system are discussed.",
author = "Hideo Tanaka and Yoshihiko Yamaguchi and Sumida, {Shin Ichi} and Manabu Kuroboshi and Misato Mochizuki and Sigeru Torii",
year = "1999",
month = "12",
day = "7",
language = "English",
pages = "3463--3468",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
number = "23",

}

TY - JOUR

T1 - Generation and reaction of copper(I) hydride in the copper(I) chloride-tributyltin hydride-NMP system

T2 - Synthesis of 3-norcephalosporin

AU - Tanaka, Hideo

AU - Yamaguchi, Yoshihiko

AU - Sumida, Shin Ichi

AU - Kuroboshi, Manabu

AU - Mochizuki, Misato

AU - Torii, Sigeru

PY - 1999/12/7

Y1 - 1999/12/7

N2 - Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of either 3-trifluoromethylsulfonyloxy-Δ3-cephem 2, allenecarboxylate 3 or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributyltin hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a copper(I) hydride species in the copper(I) chloride-tributyltin hydride-NMP or N,N-dimethylformamide (DMF) system are discussed.

AB - Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of either 3-trifluoromethylsulfonyloxy-Δ3-cephem 2, allenecarboxylate 3 or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributyltin hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a copper(I) hydride species in the copper(I) chloride-tributyltin hydride-NMP or N,N-dimethylformamide (DMF) system are discussed.

UR - http://www.scopus.com/inward/record.url?scp=0042936049&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042936049&partnerID=8YFLogxK

M3 - Article

SP - 3463

EP - 3468

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

IS - 23

ER -