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dc.contributor.authorChakraborti, AK
dc.contributor.authorKondaskar, A
dc.contributor.authorRudrawar, S
dc.date.accessioned2018-11-05T00:12:29Z
dc.date.available2018-11-05T00:12:29Z
dc.date.issued2004
dc.identifier.issn0040-4020
dc.identifier.doi10.1016/j.tet.2004.07.077
dc.identifier.urihttp://hdl.handle.net/10072/100283
dc.description.abstractMontmorillonite K 10 efficiently catalyses the opening of epoxide rings by amines in high yields with excellent regio- and diastereo-selectivities under solvent-free conditions at room temperature affording an improved process for synthesis of 2-amino alcohols. Reaction of cyclohexene oxide with aryl/alkyl amines leads to the formation of trans-2-aryl/alkylaminocyclohexanols. For unsymmetrical epoxides, the regioselectivity is controlled by the electronic and steric factors associated with the epoxide and the amine. Selective nucleophilic attack at the benzylic carbon of styrene oxide takes place with aromatic amines, whereas, aliphatic amines exhibit preferential nucleophilic attack at the terminal carbon. Aniline reacts selectively at the less hindered carbon of other unsymmetrical epoxides. The difference in the internal strain energy of the epoxide ring in cycloalkene oxides and alkene oxides led to selective nucleophilic opening of cyclohexene oxide by aniline in the presence of styrene oxide. Due to the chelation effect, selective activation of the epoxide ring in 3-phenoxy propylene oxide takes place in the presence of styrene oxide leading to preferential cleavage of the epoxide ring in 3-phenoxy propylene oxide by aniline.
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherElsevier
dc.relation.ispartofpagefrom9085
dc.relation.ispartofpageto9091
dc.relation.ispartofissue41
dc.relation.ispartofjournalTetrahedron
dc.relation.ispartofvolume60
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchBiologically active molecules
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340401
dc.subject.fieldofresearchcode3405
dc.titleScope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.hasfulltextNo Full Text
gro.griffith.authorRudrawar, Santosh


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