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Synthesis of 2‐(3‐(3,5‐bis(trifluoromethyl)phenyl)thioureido)‐3‐((dimethylamino)methyl)camphor organocatalysts
Author(s) -
Grošelj Uroš,
Ričko Sebastjan,
Svete Jurij,
Stanovnik Branko
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22035
Subject(s) - chemistry , bifunctional , camphor , thiourea , diethyl malonate , malonate , organocatalysis , trifluoromethyl , thienamycin , dimethyl malonate , michael reaction , organic chemistry , borneol , enantioselective synthesis , catalysis , medicine , alkyl , alternative medicine , traditional chinese medicine , pathology , biochemistry , antibiotics
In a stereo‐divergent synthesis, three novel camphor‐derived bifunctional thiourea organocatalysts 7 , 8 , 9 have been prepared in five steps starting from (+)‐camphor. In addition, borneol‐derived bifunctional thiourea organocatalysts 19 / 19 ’ have been prepared in three steps from (1 S )‐(+)‐camphorquinone. Novel organocatalysts 7 , 8 , 9 , 19 / 19 ’ have been evaluated in a model reaction of Michael addition of dimethyl malonate to trans ‐β‐nitrostyrene with low to moderate enantioselectivities (20%–60% ee). Configuration of all novel compounds has been meticulously determined using nuclear magnetic resonance (NMR) techniques. Chirality 24:412–419, 2012 . © 2012 Wiley Periodicals, Inc.
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