883244-66-4Relevant academic research and scientific papers
Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst
Daz-lvarez, Alba E.,Mesas-Snchez, Laura,Dinr, Peter
, p. 14273 - 14291 (2014)
The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.
Paracyclophane-based carbene-copper catalyst tuned by transannular electronic effects for asymmetric boration
Chen, Jianqiang,Duan, Wenzeng,Chen, Zhen,Ma, Manyuan,Song, Chun,Ma, Yudao
, p. 75144 - 75151 (2016/08/24)
A series of planar chiral carbene-copper complexes based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to asymmetric β-boration of α,β-unsaturated esters. As a result, transannular electronic effects of the substituent of the chiral catalyst have significant influence on the catalytic performance. A variety of chiral β-hydroxyl esters were obtained in excellent enantioselectivities (up to 97% ee) and yields (up to 99%).
(R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) catalyzed acylative kinetic resolution of racemic 3-hydroxy-3-aryl-propanoates
Yamada, Akira,Nakata, Kenya
supporting information, p. 4697 - 4701 (2016/10/03)
(R)-(+)-N-methylbenzoguanidine ((R)-NMBG) functioned as an efficient acyl transfer catalyst for the acylative kinetic resolution of racemic β-hydroxy esters using cyclohexane carboxylic anhydride under mild reaction conditions. A tert-butyl ester moiety is necessary to achieve a high selectivity. The effects of the substituents on the aromatic rings of the substrates were systematically investigated, and diverse substrates participated in the reaction with good s-values (>20) irrespective of the type of substituents and their patterns, except for o-methoxy group.
Asymmetric dehydration of β-hydroxy esters and application to the syntheses of flavane derivatives
Choi, Eui Ta,Lee, Min Hee,Kim, Yongtae,Park, Yong Sun
, p. 1515 - 1522 (2008/09/18)
Catalytic asymmetric dehydration of β-aryl or alkyl substituted β-hydroxy esters via kinetic resolution has been investigated. A brief survey of 10 different chiral ligands is conducted to examine the effects of chiral ligand structure on selectivity of t
