Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems

Anita R. Maguire; N. Rachael Buckley; Patrick O'Leary; George Ferguson

doi:10.1039/cc9960002595

Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems

Anita R. Maguire, N. Rachael Buckley, Patrick O'Leary, George Ferguson

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

28 Citations (Scopus)

Abstract

Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.

Original language	English
Pages (from-to)	2595-2596
Number of pages	2
Journal	Chemical Communications
Issue number	22
DOIs	https://doi.org/10.1039/cc9960002595
Publication status	Published - 1996
Externally published	Yes

Access to Document

10.1039/cc9960002595

Cite this

@article{743058a2617d4276adfde5f0a0e15fff,

title = "Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems",

abstract = "Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.",

author = "Maguire, \{Anita R.\} and Buckley, \{N. Rachael\} and Patrick O'Leary and George Ferguson",

year = "1996",

doi = "10.1039/cc9960002595",

language = "English",

pages = "2595--2596",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "22",

}

TY - JOUR

T1 - Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems

AU - Maguire, Anita R.

AU - Buckley, N. Rachael

AU - O'Leary, Patrick

AU - Ferguson, George

PY - 1996

Y1 - 1996

N2 - Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.

AB - Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.

UR - https://www.scopus.com/pages/publications/0002887883

U2 - 10.1039/cc9960002595

DO - 10.1039/cc9960002595

M3 - Article

SN - 1359-7345

SP - 2595

EP - 2596

JO - Chemical Communications

JF - Chemical Communications

IS - 22

ER -

Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems

Abstract

Access to Document

Other files and links

Fingerprint

Cite this