- D-Phg-L-Pro Dipeptide-derived prolinol ligands for highly enantioselective Reformatsky reactions
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Optically pure N-aminoethyl prolinol derivatives 3a-c have been prepared from the dynamic kinetic resolution of N-(α-bromo-α-phenylacetyl) proline ester 1 in asymmetric nucleophilic substitution and subsequent reduction. The peptide-derived prolinols are
- Shin, Eun-Kyoung,Kim, Hyun Jung,Kim, Yongtai,Kim, Yangmee,Park, Yong Sun
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- Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst
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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.
- Daz-lvarez, Alba E.,Mesas-Snchez, Laura,Dinr, Peter
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p. 14273 - 14291
(2014/12/11)
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- Asymmetric dehydration of β-hydroxy esters and application to the syntheses of flavane derivatives
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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
- Choi, Eui Ta,Lee, Min Hee,Kim, Yongtae,Park, Yong Sun
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p. 1515 - 1522
(2008/09/18)
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- Asymmetric dehydration of β-hydroxy esters via kinetic resolution
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Catalytic asymmetric dehydration of β-hydroxy esters via kinetic resolution has been investigated. The kinetic resolution of rac-β-hydroxy esters in the presence of prolinol chiral ligand 2a and BrZnCH2CO2t-Bu can provide highly enan
- Kim, Yongtae,Choi, Eui Ta,Lee, Min Hee,Park, Yong Sun
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p. 2833 - 2835
(2007/10/03)
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- Enantioselective reformatsky reaction induced by chiral β-amino alcohols
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Reformatsky reagent derived from tert-butyl α-bromoacetate adds to carbonyl compounds in the presence of chiral amino alcohols leading to β-hydroxy tert-butyl eaters with good e.e. The enantioface differentiation depends on the reaction conditions and on
- Andres, Jose M.,Martin, Yolanda,Pedrosa, Rafael,Perez-Encabo, Alfonso
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p. 3787 - 3794
(2007/10/03)
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