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

doi:10.1016/j.tet.2005.03.130

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

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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 language	English
Pages (from-to)	5876-5888
Number of pages	13
Journal	Tetrahedron
Volume	61
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2005.03.130
Publication status	Published - 2005

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10.1016/j.tet.2005.03.130

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@article{0eed822f4bb44c90b0533a7b52bded47,

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

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.",

author = "Buckley, {Benjamin R.} and {Bulman Page}, {Philip C.} and Harry Heaney and Sampler, {Edward P.} and Sarah Carley and Constanze Brocke and Brimble, {Margaret A.}",

year = "2005",

doi = "10.1016/j.tet.2005.03.130",

language = "English",

volume = "61",

pages = "5876--5888",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

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TY - JOUR

T1 - Use of bis-(aminol) ethers derived from N-(S)-(-)alpha-methylbenzylamine in reactions with resorcinarenes and double Mannich reactions

AU - Buckley, Benjamin R.

AU - Bulman Page, Philip C.

AU - Heaney, Harry

AU - Sampler, Edward P.

AU - Carley, Sarah

AU - Brocke, Constanze

AU - Brimble, Margaret A.

PY - 2005

Y1 - 2005

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2005.03.130

DO - 10.1016/j.tet.2005.03.130

M3 - Article

SN - 0040-4020

VL - 61

SP - 5876

EP - 5888

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -