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Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones
Author(s) -
Szántó Gábor,
Bombicz Petra,
Grün Alajos,
Kádas István
Publication year - 2008
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.20567
Subject(s) - nitromethane , chemistry , enantioselective synthesis , conjugate , chirality (physics) , aryl , stereochemistry , nitro , catalysis , organic chemistry , mathematical analysis , chiral symmetry breaking , physics , mathematics , alkyl , quantum mechanics , nambu–jona lasinio model , quark
Six active 4‐aryl‐5‐nitro‐pentan‐2‐ones were synthesized enantioselectively from the corresponding 5‐aryl‐butenones by asymmetric Michael addition of nitromethane using an imidazolidine‐type enantioselective organocatalyst. The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and crystal structure of 3,4‐methylenedioxy‐phenyl‐5‐nitro‐pentan‐2‐one has been studied by single crystal X‐ray diffraction. Chirality, 2008. © 2008 Wiley‐Liss, Inc.