71095-28-8Relevant academic research and scientific papers
β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes
Theodorou, Alexis,Papadopoulos, Giorgos N.,Kokotos, Christoforos G.
supporting information, p. 5438 - 5443 (2013/07/05)
The enantioselective α-amination reaction of α,α- disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between α,α-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding α-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to α,α-disubstituted quaternary amino acids is also described.
A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes
Chaudhuri, Rupsha,Das, Arindam,Liao, Hsin-Yi,Liu, Rai-Shung
supporting information; experimental part, p. 4601 - 4603 (2010/10/18)
A platinum-catalyzed reaction involving new aromatization/1,3-carbonyl shift cascade of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes is reported. This skeletal rearrangement is mechanistically significant because it involves a remarkable 1,3-carbonyl shift to complete the aromatization and to regenerate the catalyst.
Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
, p. 2730 - 2734 (2007/10/02)
o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
