scholarly journals Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New ChiralN-Sulfinimine

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
K. Chandra Babu ◽  
R. Buchi Reddy ◽  
E. Naresh ◽  
K. Ram Mohan ◽  
G. Madhusudhan ◽  
...  
Keyword(s):  
Antiepileptic Drug ◽  
Asymmetric Synthesis ◽  
Amino Alcohol ◽  
Enantioselective Synthesis ◽  
Ethylmagnesium Bromide

We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiralN-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiralN-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4cleavage and reduction gaveβ-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1).

A Short Enantioselective Synthesis of (S)-Levetiracetam Through Direct Pd-Catalyzed Asymmetric N-Allylation of Methyl 4-Aminobutyrate

Synlett ◽  
2021 ◽  
Author(s):  
Dominik Albat ◽  
Jörg-Martin Neudörfl ◽  
Hans-Günther Schmalz
Keyword(s):  
Antiepileptic Drug ◽  
Tartaric Acid ◽  
Enantioselective Synthesis

An exceedingly short and enantioselective synthesis of the antiepileptic drug (S)-levetiracetam was elaborated. As the chirogenic key step a Pd-catalyzed asymmetric N-allylation of methyl 4-aminobutyrate was achieved in the presence of only 1 mol% of a catalyst prepared in situ from [Pd(allyl)Cl]2 and the tartaric acid-derived C2-symmetric diphosphane ligand (S,S)-iPr-MediPhos).

Enantioselective Functionalization of Prochiral Cyclobutanones and Cyclobutenones

Synlett ◽  
2021 ◽  
Author(s):  
Memg Wang ◽  
Changxu Zhong ◽  
Ping Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Membered Ring ◽  
Enantioselective Synthesis ◽  
Ring Compounds ◽  
Recent Advances ◽  
Cyclobutane Derivatives

Enantioselective synthesis of cyclobutane derivatives is still a challenging topic in asymmetric synthesis. [2+2]-Cycloaddition and skeleton rearrangement are two primary strategies to this end. Recently, functionalization of cyclobutanones and cyclobutenones, which are readily available via [2+2]-cycloadditions as prochiral substrates, has emerged as a powerful tool to access versatile four-membered ring compounds. Herein, we summarize some recent advances in these areas from our and other groups.

scholarly journals Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones

2016 ◽  
Vol 7 (2) ◽  
pp. 1205-1211 ◽  
Author(s):  
Ryo Shintani ◽  
Ryo Takano ◽  
Kyoko Nozaki
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Synthesis ◽  
Catalytic Cycle

A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones was developed. A reasonable catalytic cycle was also experimentally established.

Enantioselective synthesis of α,α-difluoro-β-lactams using amino alcohol ligands

2014 ◽  
Vol 12 (33) ◽  
pp. 6484-6489 ◽  
Author(s):  
Atsushi Tarui ◽  
Takeshi Ikebata ◽  
Kazuyuki Sato ◽  
Masaaki Omote ◽  
Akira Ando
Keyword(s):  
Amino Alcohol ◽  
Enantioselective Synthesis ◽  
Reformatsky Reaction

A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described.

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