Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system

Zsuzsanna Sánta, P. Kolonits, József Nagy, József Nyitrai

Research output: Contribution to journalArticle

Abstract

In order to distinguish primary and secondary hydroxyl groups in the presence of a β-lactam moiety benzylidene acetal protection and reductive cleavage were used. When the reductive ring opening was carried out using diisobutylaluminium hydride, the benzylidene acetal group remained intact, while the β-lactam was reduced to the corresponding β-amino alcohol. The acetal cleavage with sodium cyanoborohydride was successful, resulting mainly in a β-lactam compound bearing the benzyloxy group on the secondary carbon atom.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalArkivoc
Volume2008
Issue number3
Publication statusPublished - 2008

Fingerprint

Lactams
Acetals
Bearings (structural)
Amino Alcohols
Hydroxyl Radical
Carbon
Atoms
nonane

Keywords

  • Benzylidene acetal
  • Protecting group
  • Reductive cleavage
  • β-Lactam

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system. / Sánta, Zsuzsanna; Kolonits, P.; Nagy, József; Nyitrai, József.

In: Arkivoc, Vol. 2008, No. 3, 2008, p. 9-16.

Research output: Contribution to journalArticle

Sánta, Z, Kolonits, P, Nagy, J & Nyitrai, J 2008, 'Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system', Arkivoc, vol. 2008, no. 3, pp. 9-16.
Sánta, Zsuzsanna ; Kolonits, P. ; Nagy, József ; Nyitrai, József. / Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system. In: Arkivoc. 2008 ; Vol. 2008, No. 3. pp. 9-16.
@article{d18909ae155646c0b5f235f03d47ba96,
title = "Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system",
abstract = "In order to distinguish primary and secondary hydroxyl groups in the presence of a β-lactam moiety benzylidene acetal protection and reductive cleavage were used. When the reductive ring opening was carried out using diisobutylaluminium hydride, the benzylidene acetal group remained intact, while the β-lactam was reduced to the corresponding β-amino alcohol. The acetal cleavage with sodium cyanoborohydride was successful, resulting mainly in a β-lactam compound bearing the benzyloxy group on the secondary carbon atom.",
keywords = "Benzylidene acetal, Protecting group, Reductive cleavage, β-Lactam",
author = "Zsuzsanna S{\'a}nta and P. Kolonits and J{\'o}zsef Nagy and J{\'o}zsef Nyitrai",
year = "2008",
language = "English",
volume = "2008",
pages = "9--16",
journal = "Arkivoc",
issn = "1551-7012",
publisher = "Arkat USA",
number = "3",

}

TY - JOUR

T1 - Regioselective ring openings in the 3,5-dioxa-8-azabicyclo-[5.2.0]nonane ring system

AU - Sánta, Zsuzsanna

AU - Kolonits, P.

AU - Nagy, József

AU - Nyitrai, József

PY - 2008

Y1 - 2008

N2 - In order to distinguish primary and secondary hydroxyl groups in the presence of a β-lactam moiety benzylidene acetal protection and reductive cleavage were used. When the reductive ring opening was carried out using diisobutylaluminium hydride, the benzylidene acetal group remained intact, while the β-lactam was reduced to the corresponding β-amino alcohol. The acetal cleavage with sodium cyanoborohydride was successful, resulting mainly in a β-lactam compound bearing the benzyloxy group on the secondary carbon atom.

AB - In order to distinguish primary and secondary hydroxyl groups in the presence of a β-lactam moiety benzylidene acetal protection and reductive cleavage were used. When the reductive ring opening was carried out using diisobutylaluminium hydride, the benzylidene acetal group remained intact, while the β-lactam was reduced to the corresponding β-amino alcohol. The acetal cleavage with sodium cyanoborohydride was successful, resulting mainly in a β-lactam compound bearing the benzyloxy group on the secondary carbon atom.

KW - Benzylidene acetal

KW - Protecting group

KW - Reductive cleavage

KW - β-Lactam

UR - http://www.scopus.com/inward/record.url?scp=39049131117&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=39049131117&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:39049131117

VL - 2008

SP - 9

EP - 16

JO - Arkivoc

JF - Arkivoc

SN - 1551-7012

IS - 3

ER -