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

Benjamin R. Buckley, Philip C. Bulman Page, Harry Heaney, Edward P. Sampler, Sarah Carley, Constanze Brocke, Margaret A. Brimble

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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.
Original languageEnglish
Pages (from-to)5876-5888
Number of pages13
JournalTetrahedron
Volume61
Issue number24
DOIs
Publication statusPublished - 2005

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