Formation of 3-azabicyclo[3.3.1]non-3-enes: Imino amides vs. imino alkenes

Ung, AT; Williams, SG; Angeloski, A; Ashmore, J; Kuzhiumparambil, U; Bhadbhade, M; Bishop, R

Formation of 3-azabicyclo[3.3.1]non-3-enes: Imino amides vs. imino alkenes

Ung, AT

Williams, SG

Angeloski, A

Ashmore, J Kuzhiumparambil, U

Bhadbhade, M Bishop, R

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Publication Type:: Journal Article
Citation:: Monatshefte fur Chemie, 2014, 145 (6), pp. 983 - 992
Issue Date:: 2014-01-01

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Field	Value	Language
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Williams, SG https://orcid.org/0000-0003-4647-436X	en_US
dc.contributor.author	Angeloski, A https://orcid.org/0000-0003-4395-1829	en_US
dc.contributor.author	Ashmore, J	en_US
dc.contributor.author	Kuzhiumparambil, U https://orcid.org/0000-0003-0582-6779	en_US
dc.contributor.author	Bhadbhade, M	en_US
dc.contributor.author	Bishop, R	en_US
dc.date.issued	2014-01-01	en_US
dc.identifier.citation	Monatshefte fur Chemie, 2014, 145 (6), pp. 983 - 992	en_US
dc.identifier.issn	0026-9247	en_US
dc.identifier.uri	http://hdl.handle.net/10453/30117
dc.description.abstract	An effective method for synthesising alkaloid-like compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereoselective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non- 3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona- 3,6-dienes (imino alkenes) were obtained in one step from (-)-β-pinene and the respective nitriles in the presence of concentrated H2SO 4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways. Graphical Abstract: [Figure not available: see fulltext.] © 2014 Springer-Verlag Wien.	en_US
dc.relation.ispartof	Monatshefte fur Chemie	en_US
dc.relation.isbasedon	10.1007/s00706-014-1185-x	en_US
dc.subject.classification	General Chemistry	en_US
dc.title	Formation of 3-azabicyclo[3.3.1]non-3-enes: Imino amides vs. imino alkenes	en_US
dc.type	Journal Article
utslib.citation.volume	6	en_US
utslib.citation.volume	145	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - C3 - Climate Change Cluster
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	6	en_US
pubs.publication-status	Published	en_US
pubs.volume	145	en_US

Abstract:

An effective method for synthesising alkaloid-like compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereoselective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non- 3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona- 3,6-dienes (imino alkenes) were obtained in one step from (-)-β-pinene and the respective nitriles in the presence of concentrated H2SO 4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways. Graphical Abstract: [Figure not available: see fulltext.] © 2014 Springer-Verlag Wien.

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http://hdl.handle.net/10453/30117