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Octa‐1,7‐diene‐4,5‐diamine Derivatives: Useful Intermediates for the Stereoselective Synthesis of Nitrogen Heterocycles and Ligands for Asymmetric Catalysis
Author(s) -
Gualandi Andrea,
Grilli Stefano,
Savoia Diego
Publication year - 2016
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.201600310
Subject(s) - chemistry , stereocenter , diene , diamine , stereoselectivity , glyoxal , allylic rearrangement , catalysis , carbene , nitrogen , reagent , enantioselective synthesis , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , natural rubber
The octa‐1,7‐diene‐4,5‐diamine skeleton is usually prepared by the addition of allylic organometallic reagents to glyoxal diimines. The relative and absolute configurations of the C4 and C5 stereocenters are dependent on the nature of the (chiral) nitrogen substituents. These compounds are useful intermediates for the construction of NHC carbene complexes and nitrogen heterocycles, such as 2,2′‐bipyrrolidines, 2,5‐diazabicyclo[2.2.1]heptanes, amino‐ and hydroxy‐substituted 7‐azanorbornane, and diamino‐substituted cyclohexanols and cyclohexanediols.