237431-63-9Relevant academic research and scientific papers
Use of bis-(aminol) ethers derived from N-(S)-(-)-α-methylbenzylamine in reactions with resorcinarenes and double Mannich reactions
Buckley, Benjamin R.,Page, Philip C. Bulman,Heaney, Harry,Sampler, Edward P.,Carley, Sarah,Brocke, Constanze,Brimble, Margaret A.
, p. 5876 - 5888 (2007/10/03)
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.
