134418-70-5Relevant articles and documents
A convenient preparation of (±)-α-methoxy-α-trifluoromethylphenylacetic acid (Mosher's acid)
Chong,Loewith
, p. 2145 - 2150 (1993)
Mosher's acid can be prepared from PhC(O)CF3 via a vinylation, methylation, ozonolysis/oxidation sequence in >80% overall yield.
Domino Synthesis of α,β-Unsaturated γ-Lactams by Stereoselective Amination of α-Tertiary Allylic Alcohols
Xie, Jianing,Xue, Sijing,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
supporting information, p. 16727 - 16731 (2018/11/23)
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions by a conceptually new and stereoselective protocol under palladium catalysis. The in situ formed Z-configured γ-amino acid cyclizes to afford an α,β-unsaturated γ-lactam, releasing water as the only byproduct. This practical catalytic transformation highlights the use of a carboxyl group acting as an activating and stereodirecting functional group to provide a wide series of pharma-relevant building blocks. Various control reactions support the crucial role of the carboxyl group in the substrate to mediate these transformations.
An enzymatic toolbox for the kinetic resolution of 2-(Pyridin-x-yl)but-3- yn-2-ols and tertiary cyanohydrins
Nguyen, Giang-Son,Kourist, Robert,Paravidino, Monica,Hummel, Anke,Rehdorf, Jessica,Orru, Romano V. A.,Hanefeld, Ulf,Bornscheuer, Uwe T.
experimental part, p. 2753 - 2758 (2010/07/06)
The kinetic resolution of a series of acetates of tertiary alcohols bearing a nitrogen substituent has been studied by using several recombinant carboxyl esterases and variants thereof expressed in E. coli. Most of the enzymes were active in the conversion of these tertiary alcohols and excellent enantioselectivities were achieved in the synthesis of three 2-(pyridin-x-yl)but-3-yn-2-ols with the nitrogen atom in the pyridine ring in the 2′-, 3′-, and 4′-positions. The resolution of tertiary cyanohydrins proved to be more difficult as the enantioselectivity of the enzymes was generally lower. Nevertheless, (S)-1-cyano-2,2,2-trifluoro-1- phenylethyl acetate was obtained with 99% ee. The results show that the limited substrate range of the individual enzymes in the synthesis of a series of tertiary alcohols can be efficiently overcome by using a combination of different enzymes.