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- Title
Chiral Mn<sup>III</sup>-salalen and -salan Complexes Derived from ( S)-Pyrrolidin-2-ylmethanamine and Their Catalytic Activity in the Asymmetric Strecker Reaction.
- Authors
Kumar, Pramod; Saravanan, S.; Khan, Noor‐ul Hasan; Hussain, Firasat; Singh, Surendra
- Abstract
The salalen and salan ligands have been synthesized by the reactions of ( S)-pyrrolidin-2-ylmethanamine and salicylaldehyde derivatives. These ligands were treated with Mn(CH3COO)2 ·4H2O followed by air oxidation to give ( S, R)-MnIII-salalen and -salan complexes in yields of 84-88 %. The absolute configuration of ( S, R)-MnIII-salalen was determined by single-crystal X-ray diffraction and CD analysis of the ligands and complexes showed similiar Cotton effects. The MnIII-salalen and -salan complexes were screened for their catalytic activity in the asymmetric Strecker reaction. ( S, R)-2,4-Di- tert-butyl-6-({[1-(3,5-di- tert-butyl-2-hydroxybenzyl)pyrrolidin-2-yl]methylimino}methyl)phenolatomanganese(III) chloride (5 mol-%) was found to be a suitable catalyst for the asymmetric Strecker reaction of N-(4-methoxybenzylidene)diphenylmethanamine with ethyl cyanoformate, which gave 89 % yield and 55 % ee of 2-(benzhydrylamino)-2-(4-methoxyphenyl)acetonitrile at -15 °C after 24 h.
- Subjects
PYRROLIDINE; CATALYTIC activity; CHEMICAL derivatives; X-ray diffraction; SINGLE crystals
- Publication
European Journal of Inorganic Chemistry, 2014, Vol 2014, Issue 29, p5077
- ISSN
1434-1948
- Publication type
Article
- DOI
10.1002/ejic.201402548