One-step multicomponent synthesis of chiral oxazolinyl-zinc complexes

• Main Authors: Mei Luo, Jing Cheng Zhang, Wen Min Pang, King Kuok Hii
• Format: Article
• Language: English
• Published: BMC 2017-08-01
• Series: Chemistry Central Journal
• Subjects: Chiral organozinc complexes; A single step; Nitriles; Chiral D/L amino alcohols,
• Online Access: http://link.springer.com/article/10.1186/s13065-017-0305-1

Abstract Background Typically, oxazolinyl metal complexes are synthesized in two steps, where the free ligand is prepared by the condensation reaction between a functionalized nitrile and an amino alcohol in the presence of a Lewis or Brønsted acid catalyst, followed by a further reaction with metal salts to obtain the corresponding metal complexes. Very often, the yield afforded by the two-step procedure is not high, and very few oxazolinyl zinc complexes have been prepared by this route. Given that metal-oxazoline complexes often contain Lewis acidic metals, it is conceivable that the two steps may be telescoped. Results A series of novel chiral organozinc complexes 1–15 were assembled in a single step, All crystalline compounds were fully characterized, including the report of 15 X-ray crystal structures, including a wide structural diversity. Conclusions A series of novel chiral organozinc complexes were assembled in a single step, from nitriles, chiral D/L amino alcohols, and a stoichiometric amount of ZnCl2, with moderate to high yields (20–90%). Graphical abstract A series of novel chiral organozinc complexes can be assembled in moderate to high yields (20–90%), from a mixture of nitriles, chiral amino alcohols and ZnCl2. All crystalline compounds were fully characterized, including the report of 15 X-ray crystal structures, including a wide structural diversity.