91828-70-5Relevant academic research and scientific papers
Synthesis and Applications of Unquaternized C-Bound Boron Enolates
Ng, Elvis Wang Hei,Low, Kam-Hung,Chiu, Pauline
supporting information, p. 3537 - 3541 (2018/03/21)
A general and facile method to prepare unquaternized C-bound boron enolates by a ligand-controlled O-to-C isomerization is reported. Using this protocol, C-bound pinacolboron enolates have been isolated in pure form for the first time, and have been fully characterized by NMR spectroscopy and X-ray crystallography. In contrast to the general perception, such C-boron enolates are stable without coordinative saturation at the boron. Moreover, C-boron enolates present reactivities that are distinct from the O-boron enolates, and their applications in C-O and C-C bond formations are demonstrated.
Uncatalyzed and Chorismate Mutase Catalyzed Claisen Rearrangement of (Z)-9-Methylchorismic Acid
Lesuisse, Dominique,Berchtold, Glenn A.
, p. 4992 - 4997 (2007/10/02)
A synthesis of (-)- and (+/-)-(Z)-9-methylchorismic acid (3) is reported.The half-life for the uncatalyzed Claisen rearrangement of (+/-)-3 in H2O (pH 7.5, 30 deg C) is 5.7 h.Chorismate analogue (-)-3 was a modest substrate for chorismate mutase (chorismate mutase-prephenate dehydrogenase from E. coli): Km = 4.0 mM, kcat./kuncat. = 4.2*104.It was established that the enzyme-catalyzed Claisen rearrangement of (-)-3 proceeds through a chairlike transition state in similar fashion to the chorismate mutase catalyzed rearrangement of (-)-chorismic acid (1).
The Use of Microorganisms in Organic Synthesis. IV. Microbiological Asymmetric Reduction of Methyl 3-Phenyl 2-Oxobutyrate
Akita, Hiroyuki,Furuichi, Akiya,Koshiji, Hiroko,Horikoshi, Koki,Oishi, Takeshi
, p. 1342 - 1348 (2007/10/02)
The synthesis of optically active α-hydroxy β-methyl esters V by means of microbiological reduction of the corresponding α-keto β-methyl esters IV was carried out.Methyl 3-phenyl-2-oxobutyrate 3 was found to be reduced by a variety of yeasts to the α-hydr
