Premium
Design and Development of Bioinspired Guanine‐Based Organic Catalyst for Asymmetric Catalysis
Author(s) -
Suez Gal,
Bloch Victoria,
Nisnevich Gennady,
Gandelman Mark
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.201200118
Subject(s) - chemistry , catalysis , bifunctional , nucleobase , guanine , combinatorial chemistry , hydrogen bond , conjugate , organic synthesis , enantioselective synthesis , organic chemistry , dna , molecule , nucleotide , mathematical analysis , biochemistry , mathematics , gene
Design, preparation, and studies of a family of new organic catalysts are presented. The design of the catalysts is inspired by the ability of DNA nucleobases to develop precise and explicit hydrogen bonds. We have shown that this phenomenon can be used to create a useful organic catalyst that demonstrates a recognition pattern similar to those of common organic substrates. A selected bifunctional catalyst based on a guanine structure has been shown to catalyze the conjugate addition of 1,3‐dicarbonyl compounds to various nitroalkenes, providing the products in good yields and enantioselectivities.