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  4. Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*,3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy)buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction
 
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Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*,3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy)buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction

Auteur(s)
Vallat, Olivier
Buciumas, Ana-Maria 
Institut de chimie 
Neier, Reinhard 
Institut de chimie 
Stoeckli-Evans, Helen 
Institut de physique 
Date de parution
2010
In
J. Chem. Crystallogr.
Vol.
1
No
40
De la page
10
A la page
14
Mots-clés
  • Chiral induction (Felkin-Anh
  • stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • Ethers Role: PEP (Physical
  • engineering or chemical process)
  • RCT (Reactant)
  • PROC (Process)
  • RACT (Reactant or reagent) (enol
  • silyl
  • stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • Dimers Role: FMU (Formation
  • unclassified)
  • PEP (Physical
  • engineering or chemical process)
  • PRP (Properties)
  • FORM (Formation
  • nonpreparative)
  • PROC (Process) (hydrogen-bonded
  • stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • Aldol addition (stereoselective
  • stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • Chemical chains
  • Crystal structure
  • Hydrogen bond
  • Molecular structure
  • Mukaiyama aldol reaction
  • Stereochemistry
  • Supramolecular structure
  • Transition state structure (stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • Hydrogen bond (weak
  • stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R*
  • 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R*
  • 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate)
  • rac ethylchlorohydroxyphenylbuthanethioate ethylphenyltosyloxybuthanethioate dichotomy stereoselectivity Mukaiyama crossed aldol crystallog
  • Chiral induction (Fel...

  • stereoselectivity dic...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • Ethers Role: PEP (Phy...

  • engineering or chemic...

  • RCT (Reactant)

  • PROC (Process)

  • RACT (Reactant or rea...

  • silyl

  • stereoselectivity dic...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • Dimers Role: FMU (For...

  • unclassified)

  • PEP (Physical

  • engineering or chemic...

  • PRP (Properties)

  • FORM (Formation

  • nonpreparative)

  • PROC (Process) (hydro...

  • stereoselectivity dic...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • Aldol addition (stere...

  • stereoselectivity dic...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • Chemical chains

  • Crystal structure

  • Hydrogen bond

  • Molecular structure

  • Mukaiyama aldol react...

  • Stereochemistry

  • Supramolecular struct...

  • Transition state stru...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • Hydrogen bond (weak

  • stereoselectivity dic...

  • 3R*)-S-ethyl-4-chloro...

  • 3R*)-S-ethyl-2-phenyl...

  • rac ethylchlorohydrox...

Résumé
The compds., rac-(2R*,3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate (I) and rac-(2R*,3R*)-S-ethyl-3-hydroxy-2-phenylbuthanethioate (II), were prepd. by the Mukaiyama crossed aldol reaction between the silyl enol ether of S-Et 2-phenylethanethioate and simple aldehydes, like 2-chloroacetaldehyde (for I) and acetaldehyde (for II). The stereoselectivity of the Mukaiyama aldol reaction has switched from a syn selective process for the reaction using 2-chloroacetaldehyde to an anti selective process for the reaction with acetaldehyde. [on SciFinder(R)]
Identifiants
https://libra.unine.ch/handle/123456789/21467
Type de publication
journal article
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