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Crystallization‐Driven Asymmetric Synthesis of Pyridine‐β‐nitroalcohols via Discovery‐Oriented Self‐Resolution of a Dynamic System
Author(s) -
Angelin Marcus,
Vongvilai Pornrapee,
Fischer Andreas,
Ramström Olof
Publication year - 2010
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.201000907
Subject(s) - crystallization , pyridine , chemistry , resolution (logic) , combinatorial chemistry , drug discovery , nanotechnology , organic chemistry , computer science , materials science , artificial intelligence , biochemistry
The study of dynamic nitroaldol systems aided the discovery of a diastereoselective crystallization process through amplification of 2‐nitro‐1‐(pyridine‐4‐yl)propan‐1‐ol. The phenomenon was further developed into an effective procedure for asymmetic synthesis of pyridine‐nitroalcohols and several substrates were screened to this end. These results demonstrate how work with larger dynamic systems facilitates and increases the likelihood of serendipitous discoveries.