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A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the α,β-unsaturated sulfoxide derived from (R)-glyceraldehyde acetonide

✍ Scribed by Dawei Ma; Bin Zou; Wei Zhu; Huadong Xu


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
216 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


Diastereoselective Michael addition of ammonia to sulfoxide 3a derived from (R)-glyceraldehyde acetonide provides amine 4a, which is converted into Nelfinavir using BF 3 •Et 2 O/NaI reduction and subsequent coupling reactions as key steps.