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Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts
Author(s) -
Ričko Sebastijan,
Golobič Amalija,
Svete Jurij,
Stanovnik Branko,
Grošelj Uroš
Publication year - 2015
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.22386
Subject(s) - bifunctional , thiourea , chemistry , camphor , catalysis , diethyl malonate , dimethyl malonate , organocatalysis , malonate , organic chemistry , enantioselective synthesis , michael reaction , combinatorial chemistry
Synthesis and catalyst performance of 2,3‐ (types B and C ) and 2,8‐disubstituted (type D ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type B has, so far, not been realized, while catalysts of type C , i.e ., the 2,3‐ exo ‐ and the 2‐ endo ‐3‐ exo ‐thiourea catalysts, were prepared in six steps starting from (+)‐camphor. The catalysts of type D were prepared from (+)‐camphor in eight steps. All the potential catalysts as well as most of the intermediate products were carefully structurally characterized. The thiourea bifunctional organocatalysts were tested in a model reaction of Michael addition of dimethyl malonate to trans ‐β‐nitrostyrene. Chirality 27:39–52, 2015 . © 2014 Wiley Periodicals, Inc.