Development of a Two-Step, Enantioselective Synthesis of an Amino Alcohol Drug Candidate

2015 ◽  
Vol 19 (9) ◽  
pp. 1317-1322 ◽  
Author(s):  
Michael A. Schmidt ◽  
Emily A. Reiff ◽  
Xinhua Qian ◽  
Chao Hang ◽  
Vu Chi Truc ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Enantioselective Synthesis ◽  
Drug Candidate

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.

Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction.

ChemInform ◽  
2004 ◽  
Vol 35 (6) ◽  
Author(s):  
Peter Pojarliev ◽  
William T. Biller ◽  
Harry J. Martin ◽  
Benjamin List
Keyword(s):  
Mannich Reaction ◽  
Amino Alcohol ◽  
Enantioselective Synthesis

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).

scholarly journals Enantioselective Synthesis of Optically Pure Amino Alcohol Derivatives by Yeast Reduction

1987 ◽  
Vol 16 (1) ◽  
pp. 129-132 ◽  
Author(s):  
Tamotsu Fujisawa ◽  
Hiroki Hayashi ◽  
Yoshino Kishioka
Keyword(s):  
Amino Alcohol ◽  
Enantioselective Synthesis ◽  
Optically Pure

Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 60-64
Author(s):  
Yun Zhou ◽  
Lifeng Wang ◽  
Shuoning Li ◽  
Sijie Ma ◽  
Patrick J. Walsh ◽  
...  
Keyword(s):  
Functional Groups ◽  
Amino Alcohol ◽  
Carbon Chain ◽  
Enantioselective Synthesis ◽  
Asymmetric Addition ◽  
Enantioselective Addition

A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.

Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction

Synlett ◽  
2003 ◽  
pp. 1903-1905 ◽  
Author(s):  
Benjamin List ◽  
Peter Pojarliev ◽  
William T. Biller ◽  
Harry J. Martin
Keyword(s):  
Mannich Reaction ◽  
Amino Alcohol ◽  
Enantioselective Synthesis

ChemInform Abstract: Enantioselective Synthesis of α,α-Difluoro-β-lactams Using Amino Alcohol Ligands.

ChemInform ◽  
2014 ◽  
Vol 46 (2) ◽  
pp. no-no
Author(s):  
Atsushi Tarui ◽  
Takeshi Ikebata ◽  
Kazuyuki Sato ◽  
Masaaki Omote ◽  
Akira Ando
Keyword(s):  
Amino Alcohol ◽  
Enantioselective Synthesis
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