Use of Bis(aminol) Ethers derived from N-(S)-(-)-a-Methylbenzylamine in Reactions with Resorcinarenes and Double Mannich Reactions

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dc.contributor.author Brimble, MA en
dc.contributor.author Buckley, BR en
dc.contributor.author Bulman Page, PC en
dc.contributor.author Heaney, H en
dc.contributor.author Sampler, EP en
dc.contributor.author Carley, Sarah en
dc.contributor.author Brocke, Constanze en
dc.date.accessioned 2011-09-21T23:37:23Z en
dc.date.issued 2005 en
dc.identifier.citation TETRAHEDRON 61(24):5876-5888 13 Jun 2005 en
dc.identifier.issn 0040-4020 en
dc.identifier.uri http://hdl.handle.net/2292/8258 en
dc.description.abstract The synthesis of some chiral bis-(aminol)ethers are described. Reaction of a solution of the resorcin[4]arene derived from propanal with N,N-bis(methoxymethyl)-N-(S)-(−)-α-methylbenzylamine in toluene at 85 °C initially afforded a 1:1 mixture of two diastereoisomeric tetrakis(benzoxazines). Further, heating of this mixture under reflux in ethanol for 24 h afforded the crystalline (αS),(S)-diastereoisomer in 77% yield. N,N-bis(ethoxymethyl)-N-(S)-(−)-α-methylbenzylamine and N,N-bis(ethoxymethyl)-N-(R)-(+)-α-methylbenzylamine were reacted with β keto esters to afford a 1:1 mixture of the diastereoisomeric double Mannich adducts. Two of the double Mannich adducts were converted into tricyclic ABE analogues of the alkaloid methyllycaconitine 1. en
dc.language EN en
dc.publisher Elsevier Ltd. en
dc.relation.ispartofseries Tetrahedron en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0040-4020/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject chiral bis-(aminol) ether en
dc.subject Mannich reaction en
dc.subject resorcinarenes en
dc.subject methyllycaconitine en
dc.subject RING-E ANALOGS en
dc.subject BIS(AMINOL) ETHERS en
dc.subject NMR-SPECTROSCOPY en
dc.subject METHYLLYCACONITINE en
dc.subject DERIVATIVES en
dc.subject AMINES en
dc.subject RESORCARENES en
dc.subject RECEPTORS en
dc.subject ACID en
dc.title Use of Bis(aminol) Ethers derived from N-(S)-(-)-a-Methylbenzylamine in Reactions with Resorcinarenes and Double Mannich Reactions en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.tet.2005.03.130 en
pubs.issue 24 en
pubs.begin-page 5876 en
pubs.volume 61 en
dc.rights.holder Copyright: 2005 Elsevier Ltd. en
pubs.end-page 5888 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 39893 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en


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