Journal article
Asymmetric Synthesis using Sulfinimines (Thiooxime S-Oxides)
Phosphorus, sulfur, and silicon and the related elements, v 120(1), pp 291-303
01 Jan 1997
Abstract
The addition of diethylaluminum cyanide and the lithium enolate of methyl α-bromoacetate to sulfinimines (thiooxime S-oxides) is highly diastereoselective affording α-amino nitriles and N-sulfinylaziridines, respectively. Hydroloysis of the α-amino nitriles gives α-amino acids in high ee, while hydrolysis of N-sulfinylaziridine carboxylic acids give β-hydroxy-α-amino acids. The latter compounds were transformed into (+)-thiamphenicol, a broad spectrum antibiotic and sphingosine, an important component of the sphingolipids.
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15 citations in Scopus
Details
- Title
- Asymmetric Synthesis using Sulfinimines (Thiooxime S-Oxides)
- Creators
- Franklin A. Davis - Temple UniversityPadma S. Portonovo - Temple UniversityRajarathnam E. Reddy - Temple UniversityG. Venkat Reddy - Temple UniversityPing Zhou - Temple University
- Publication Details
- Phosphorus, sulfur, and silicon and the related elements, v 120(1), pp 291-303
- Publisher
- Taylor & Francis Group
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Scopus ID
- 2-s2.0-0031483042
- Other Identifier
- 991019173747604721