Enantioselective Synthesis of Antiepileptic Drug : (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine
Joint Authors
Mukkanti, K.
Naresh, E.
Buchi Reddy, R.
Ram Mohan, K.
Madhusudhan, G.
Chandra Babu, K.
Source
Issue
Vol. 2013, Issue 2013 (31 Dec. 2013), pp.1-6, 6 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2012-06-14
Country of Publication
Egypt
No. of Pages
6
Main Subjects
Abstract EN
We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiral N-sulfinimine (3).
The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity.
Simultaneous deprotection and deacetylation followed by NaIO4 cleavage and reduction gave β-amino alcohol (6).
Subsequent reactions yielded the targeted compound levetiracetam (1).
American Psychological Association (APA)
Chandra Babu, K.& Buchi Reddy, R.& Naresh, E.& Ram Mohan, K.& Madhusudhan, G.& Mukkanti, K.. 2012. Enantioselective Synthesis of Antiepileptic Drug : (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine. Journal of Chemistry،Vol. 2013, no. 2013, pp.1-6.
https://search.emarefa.net/detail/BIM-474482
Modern Language Association (MLA)
Chandra Babu, K.…[et al.]. Enantioselective Synthesis of Antiepileptic Drug : (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine. Journal of Chemistry No. 2013 (2013), pp.1-6.
https://search.emarefa.net/detail/BIM-474482
American Medical Association (AMA)
Chandra Babu, K.& Buchi Reddy, R.& Naresh, E.& Ram Mohan, K.& Madhusudhan, G.& Mukkanti, K.. Enantioselective Synthesis of Antiepileptic Drug : (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine. Journal of Chemistry. 2012. Vol. 2013, no. 2013, pp.1-6.
https://search.emarefa.net/detail/BIM-474482
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-474482