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Organocatalysed Asymmetric β‐Amination and Multicomponent syn ‐Selective Diamination of α,β‐Unsaturated Aldehydes
Author(s) -
Jiang Hao,
Nielsen Johanne B.,
Nielsen Martin,
Jørgensen Karl Anker
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700696
Subject(s) - chemistry , amination , diethyl azodicarboxylate , amine gas treating , pyrrolidine , optically active , succinimide , stereoselectivity , organocatalysis , organic chemistry , catalysis , combinatorial chemistry , enantioselective synthesis , triphenylphosphine
An easy and affordable route for obtaining chiral β‐aminated‐ and α,β‐diaminated aldehydes, 1,3‐aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine ( S )‐2‐[bis(3,5‐bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate α,β‐unsaturated aldehydes, which allows succinimide to add in a 1,4‐regio‐ and stereoselective fashion thereby forming N‐protected 1,3‐aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3‐aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active α,β‐ syn ‐diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one‐pot reaction.