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Primary Amine‐Thioureas with Improved Catalytic Properties for “Difficult” Michael Reactions: Efficient Organocatalytic Syntheses of ( S )‐Baclofen, ( R )‐Baclofen and ( S )‐Phenibut
Author(s) -
Tsakos Michail,
Kokotos Christoforos G.,
Kokotos George
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100636
Subject(s) - chemistry , catalysis , baclofen , amine gas treating , organocatalysis , organic chemistry , michael reaction , primary (astronomy) , derivative (finance) , combinatorial chemistry , agonist , enantioselective synthesis , biochemistry , physics , receptor , astronomy , financial economics , economics
Among the class of primary amine‐thioureas based on tert ‐butyl esters of α‐amino acids, the most efficient organocatalyst for “difficult” Michael reactions was identified. The derivative based on ( S )‐di‐ tert ‐butyl aspartate and (1 R ,2 R )‐diphenylethylenediamine provided the products of the reaction between aryl methyl ketones and nitroolefins in excellent yields and enantioselectivities. In addition, this new catalyst can be used at low catalyst loading (5 mol%). The utility of this methodology was highlighted by the efficient synthesis of ( S )‐baclofen, ( R )‐baclofen and ( S )‐phenibut.