1616632-81-5Relevant academic research and scientific papers
Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones
Chaudhari, Dipali A.,Fernandes, Rodney A.
, p. 2113 - 2121 (2016/03/15)
A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.
Stereoselective Access to 1-[2-Bromo(het)aryloxy]propan-2-amines Using Transaminases and Lipases; Development of a Chemoenzymatic Strategy Toward a Levofloxacin Precursor
Mourelle-Insua, ángela,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 9765 - 9774 (2016/10/31)
Two independent enzymatic strategies have been developed toward the synthesis of enantioenriched 1-[2-bromo(het)aryloxy]propan-2-amines. With that purpose a series of racemic amines and prochiral ketones have been synthesized from commercially available 2-bromophenols or brominated pyridine derivatives bearing different pattern substitutions in the aromatic ring. Biotransamination experiments have been studied using ketones as starting materials, yielding both the (R)- and (S)-amine enantiomers with high selectivity (91-99% ee) depending on the transaminase source. In a complementary approach, the classical kinetic resolutions of the racemic amines have been investigated using Candida antarctica lipase type B as biocatalyst. Ethyl methoxyacetate was found as a suitable acyl donor leading to the corresponding (S)-amines (90-99% ee) and (R)-amides (88-99% ee) with high selectivity in most of the cases. A preparative biotransamination process has been developed for the synthesis of (2S)-1-(6-bromo-2,3-difluorophenoxy)propan-2-amine in 61% isolated yield after 24 h, a valuable precursor of the antimicrobial agent Levofloxacin.
Synthesis of methyl ketones from terminal olefins using PdCl 2/CrO3 system mimicking the Wacker process
Fernandes, Rodney A.,Bethi, Venkati
, p. 4760 - 4767 (2014/06/24)
An efficient synthesis of methyl ketones from terminal olefins using PdCl2/CrO3 system mimicking the Wacker process is developed. The method shows good functional groups compatibility, no aldehyde by-products and is operationally simple. CrO3 is the sole oxidant and replaces both Cu-salts and molecular oxygen, traditionally used in this process. The method holds potential for future applications in organic synthesis.
