Use of bis-(aminol) ethers derived from N-(S)-(-)alpha-methylbenzylamine in reactions with resorcinarenes and double Mannich reactions

Buckley, Benjamin R., Bulman Page, Philip C., Heaney, Harry, Sampler, Edward P., Carley, Sarah, Brocke, Constanze and Brimble, Margaret A. (2005) Use of bis-(aminol) ethers derived from N-(S)-(-)alpha-methylbenzylamine in reactions with resorcinarenes and double Mannich reactions. Tetrahedron, 61 (24). pp. 5876-5888. ISSN 0040-4020

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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)-(-)-alpha-methylbenzylamine in toluene at 85 degrees 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 (alpha S),(S)-diastereoisomer in 77% yield. N,N-bis(ethoxymethyl)-N-(S)-(-)-alpha-methylbenzylamine and N,N-bis(ethoxymethyl)-N-(R)-(+)-alpha-methylbenzylamine were reacted with beta 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. (c) 2005 Elsevier Ltd. All rights reserved.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	20 Jun 2011 15:40
Last Modified:	24 Sep 2024 09:56
URI:	https://ueaeprints.uea.ac.uk/id/eprint/32862
DOI:	10.1016/j.tet.2005.03.130

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