146452-39-3Relevant academic research and scientific papers
Stereoselective, biocatalytic reductions of α-chloro-β-keto esters
Kaluzna, Iwona A.,Feske, Brent D.,Wittayanan, Weerawut,Ghiviriga, Ion,Stewart, Jon D.
, p. 342 - 345 (2005)
(Chemical Equation Presented). Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of α-chloro-β-keto esters. In nearly all cases, it was possible to produce at least two of t
Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination
De Schutter, Coralie,Sari, Ozkan,Coats, Steven J.,Amblard, Franck,Schinazi, Raymond F.
, p. 13171 - 13178 (2017/12/26)
A novel and efficient route for the preparation of (2S)-2-chloro-2-fluorolactone 29 is described. This approach takes advantage of a highly efficient diastereoselective electrophilic fluorination reaction (94% yield; >50:1 dr)
Asymmetric reduction of 2-chloro-3-oxo esters by transfer hydrogenation
Bai, Jinjin,Miao, Shifeng,Wu, Yun,Zhang, Yawen
experimental part, p. 2476 - 2480 (2012/02/04)
Asymmetric reduction of 2-chloro-3-oxo esters was achieved by catalytic transfer hydrogenation using [RuCl2(p-cymene)](S,S)-TsDPEN as the chiral catalyst and HCOOH-Et3N as the hydrogen source. Moderate to good yields (up to 85%) and
A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: Dynamic reductive kinetic resolution entry into the Taxotere side chain
Applegate, Gregory A.,Cheloha, Ross W.,Nelson, David L.,Berkowitz, David B.
, p. 2420 - 2422 (2011/04/15)
An NADP-dependent alcohol dehydrogenase from Clostridium acetobutylicum (CaADH) has been expressed and characterized. CaADH enantioselectively reduces aromatic α-, β- and γ-keto esters to the corresponding d-hydroxy esters and provides a building block for the Taxotere side chain (95% yield, 95% de, 99% ee) by dynamic reductive kinetic resolution (DYRKR).
Enantiodivergent, biocatalytic routes to both taxol side chain antipodes
Feske, Brent D.,Kaluzna, Iwona A.,Stewart, Jon D.
, p. 9654 - 9657 (2007/10/03)
Two enantiocomplementary bakers' yeast enzymes reduced an α-chloro-β-keto ester to yield precursors for both enantiomers of the N-benzoyl phenylisoserine Taxol side chain. After base-mediated ring closure of the chlorohydrin enantiomers, the epoxides were
Synthesis of (2R,3S)-isobutyl phenylisoserinate, the Taxol() side chain, from ethyl benzoylacetate
Wuts, Peter G. M.,Gu, Rui Lin,Northuis, Jill M.
, p. 2117 - 2123 (2007/10/03)
Reduction of ethyl 2-chloro-3-phenyl-3-oxopropionate with borohydride affords predominately the syn-chlorohydrin. Resolution of this ester with the lipase MAP-10 gives (2S,3R)-2-chloro-3-hydroxypropionic acid which after esterification with MeOH/HCl is co
The reactions of α,β-unsaturated esters by HCL/DMF/oxone system
Son, Ji Suk,Jung, Keum Shin,Kim, Hyoung Rae,Kim, Jae Nyoung
, p. 1847 - 1855 (2007/10/03)
The reactions of α,β-unsaturated esters by HCl/DMF/Oxone system afforded four different chlorinated products 2-5 in variable yields.
The microbial reduction of 2-chloro-3-oxoesters
Cabon,Buisson,Larcheveque,Azerad
, p. 2199 - 2210 (2007/10/03)
Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.
A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes
Genet, Jean-Pierre,Cano De Andrade,Ratovelomanana-Vidal
, p. 2063 - 2066 (2007/10/02)
2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (II) catalysts prepared in-situ from (COD)Ru(2-methylallyl)2 in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%, 2-chloro-3-hydroxy esters were treated with different bases to give (E)-and (Z)-2,3-epoxyalkanoates in 65-90% yields with 84-97% ee.
Microbial reduction of 2-chloro-3-aryl-3-oxopropionic acid esters
Cabon,Larcheveque,Buisson,Azerad
, p. 7337 - 7340 (2007/10/02)
2-Chloro-3-aryl-3-oxopropionic acid esters are reduced by microorganisms to syn- and/or anti-2-chloro-3-hydroxy-3-arylpropionates, in competition with dechlorination and decarboxylation reactions. Using selected strains, it is possible to obtain enantiomerically pure chlorohydroxyesters, which were converted to the corresponding phenylglycidic esters with high stereospecificity.
