Asymmetric Henry reaction catalysed by L- proline derivatives in the presence of Cu( OAc) (2): isolation and characterization of an in situ formed Cu( II) complex

作者：Sema H Atoholi; Bez Ghanashyam^*; Karmakar Sanjib

来源：Applied Organometallic Chemistry, 2014, 28(4): 290-297.

DOI：10.1002/aoc.3123

• Henry reaction
• -nitroalcohol
• asymmetric
• L-proline
• copper(II) acetate

Synthesis of asymmetric -nitroalcohols by the Henry reaction is one of the most exploited carbon-carbon bond-forming reactions owing to the versatility of both functional groups for synthetic manipulation by functional group interconversion. Here we report synthesis of a series of proline-derived compounds to study their catalytic activities for asymmetric Henry reaction in the presence of Cu(OAc)(2).H2O. The proline derivative, 2-((E)-(((S)-1-benzylpyrrolidinyl)diphenylmethylimino)methyl)phenol 1 showed optimum catalytic activity. The catalytic species Cu(II)-1 complex, formed in situ, was isolated and characterized by various spectroscopic techniques and X-ray crystallography to show a cis-N2O2 coordination geometry. Asymmetric -nitroalcohols were achieved without the use of added base, unlike most of the reported protocols.

• 出版日期2014-4