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Stereoselective Synthesis of cis , cis ‐Configured Vicinal Triamines
Author(s) -
Schulte Adrian,
Saito Susumu,
Wünsch Bernhard
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402685
Subject(s) - stereoselectivity , chemistry , aminal , imine , vicinal , isomerization , stereochemistry , amine gas treating , organic chemistry , catalysis
The first stereoselective synthesis of a cis , cis ‐configured vicinal triamine was achieved, starting from N ‐cyclohexenylpyrrolidone ( 10 ). The reaction sequence consists of the stereoselective construction of the trans ‐configured 1,3‐diamide 14 , trans ‐to‐ cis isomerization via enols or enamines, and subsequent highly stereoselective reduction of the intermediate imine 17D to the amine 18A . The postulated reaction pathway explains the observed stereoconvergence and is supported by calculation of the heats of formation of its intermediates at the PM3 level. LiAlH 4 reduction of 18A yielded the tetracyclic aminal 19 , which was converted into the pyrrolidinylquinoxaline 7 , which showed low to moderate affinity towards κ and σ 1 receptors.