enantioselective synthesis of antiepileptic drug: (-)-levetiracetam—synthetic applications of the versatile new chiral n-sulfinimine
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2013
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Abstract
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).
| Reference Key |
babu2013journalenantioselective
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| Authors | ;K. Chandra Babu;R. Buchi Reddy;E. Naresh;K. Ram Mohan;G. Madhusudhan;K. Mukkanti |
| Journal | british journal of psychology (london, england : 1953) |
| Year | 2013 |
| DOI |
10.1155/2013/475032
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