Journal ArticleDOI
Enantioselective synthesis of β-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(−)-baclofen
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TLDR
In this paper, a three-step synthesis of (R)-(−)-baclofen is described, where the key step is the orthoester Claisen rearrangement of enantiopure allylic alcohol (S,E)- (−)- 1a, affording γ,δ-unsaturated ester with high stereoselectivity.Abstract:
A three step synthesis of (R)-(−)-baclofen is described. The key step is the orthoester Claisen rearrangement of enantiopure allylic alcohol (S,E)-(−)- 1a , affording γ,δ-unsaturated ester (S,E)-(+)- 6 with high stereoselectivity. This latter derivative is converted into ( R )-(−)-baclofen through a high yield one-pot reaction.read more
Citations
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Reductive Amination in the Synthesis of Pharmaceuticals.
Oleg I. Afanasyev,Ekaterina A. Kuchuk,Dmitry L. Usanov,Denis Chusov,Denis Chusov,Denis Chusov +5 more
TL;DR: This Review concisely compiles information on 71 medical substances that are synthesized by reductive amination according to the principle of action and a general synthetic scheme is provided for each compound.
Journal ArticleDOI
Organocatalytic enantioselective acyl transfer onto racemic as well as meso alcohols, amines, and thiols.
TL;DR: This Review examines and highlights recent developments in acyl transfer and utilizes acylation reactions as a practical way for stereoselection and functional-group protection.
Journal ArticleDOI
Stereoselective synthesis of γ-amino acids
Mario Ordóñez,Carlos Cativiela +1 more
TL;DR: An overview of synthetic approaches to linear and cyclic chiral γ-amino acids and derivatives is presented in this article, where data on the practical applications of these acids are also discussed.
Journal ArticleDOI
Enantioselective Michael Addition of Nitromethane to α,β-Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (R)-Baclofen
E. J. Corey,Fu-Yao Zhang +1 more
TL;DR: Enantioselective Michael addition of nitromethane to an α,β-enone is a key step in the synthesis of (R)-baclofen.
Journal ArticleDOI
Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
TL;DR: Ruthenium hydride 14 appeared to be a key species in the racemization of (S)-1-phenylethanol with 4 and potassium tert-butoxide, and at room temperature, not only simple alcohols but also functionalized ones such as allyliccohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates.
References
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Journal ArticleDOI
Quantitative analyses of biochemical kinetic resolutions of enantiomers
Journal ArticleDOI
Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene
William S. Johnson,Lucius Werthemann,William R. Bartlett,Timothy J. Brocksom,Tsung-Tee Li,D. John Faulkner,Michael R. Petersen +6 more
Journal ArticleDOI
The biological activity of d-baclofen (Lipresal®)
TL;DR: Racemic and l-baclofen partly antagonized electro-ionotrophoretically and it was conlcuded that the biologica activity of bacl ofen resides with the l-enantiomer.
Journal ArticleDOI
Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals
TL;DR: An efficient and general enantioselective synthesis of β-alkyl-γ-butyrolactones has been developed using an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity.
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Enantioselective Michael Addition of Nitromethane to α,β-Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (R)-Baclofen
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