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Microwave‐Assisted Synthesis of Guanidine Organocatalysts Bearing a Tetrahydroisoquinoline Framework and Their Evaluation in Michael Addition Reactions
Author(s) -
Naicker Tricia,
Arvidsson Per I.,
Kruger Hendrik G.,
Maguire Glenn E. M.,
Govender Thavendran
Publication year - 2012
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.201200303
Subject(s) - guanidine , chemistry , michael reaction , tetrahydroisoquinoline , amide , yield (engineering) , organocatalysis , microwave chemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , microwave irradiation , materials science , metallurgy
The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and β‐keto esters with nitro‐olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave‐assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee ).