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A Three‐Component Reaction Based on a Remote‐Group‐Directed Dynamic Kinetic Aza‐Michael Addition: Stereoselective Synthesis of Imidazolidin‐4‐ones
Author(s) -
Xu Zhenghu,
Buechler Tyler,
Wheeler Kraig,
Wang Hong
Publication year - 2010
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.200903508
Subject(s) - michael reaction , stereoselectivity , aldehyde , amide , component (thermodynamics) , chemistry , computer science , stereochemistry , combinatorial chemistry , organic chemistry , physics , thermodynamics , catalysis
In control : An α‐amino amide reacted with an aldehyde and a Michael acceptor to form stable imidazolidin‐4‐ones with high stereoselectivity. A dynamic kinetic aza‐Michael addition was discovered and applied to the three‐component reaction to enforce high stereoselectivity. A remote group was incorporated to invert the reaction process and direct the reaction towards the desired product (see scheme).