Asymmetric synthesis using sulfinimines (thiooxime S-oxides)

Article abstract of DOI:10.1080/10426509708545525

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. Hydrolysis 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.

Full text of DOI:10.1080/10426509708545525

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Phosphorus, Sulfur, and Silicon
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Asymmetric Synthesis using
Sulfinimines (Thiooxime S-Oxides)
Franklin A. Davis , Padma S. Portonovo , Rajarathnam E.
Reddy , G. Venkat Reddy & Ping Zhou
a Department of Chemistry, Temple University,
Philadelphia, PA 19122
b Department of Chemistry, Temple University,
Philadelphia, PA 19122
c Department of Chemistry, Temple University,
Philadelphia, PA 19122
d Department of Chemistry, Temple University,
Philadelphia, PA 19122
e Department of Chemistry, Temple University,
Philadelphia, PA 19122
Version of record first published: 17 Mar 2008.
To cite this article: Franklin A. Davis , Padma S. Portonovo , Rajarathnam E. Reddy , G.
Venkat Reddy & Ping Zhou (1997): Asymmetric Synthesis using Sulfinimines (Thiooxime S-
Oxides), Phosphorus, Sulfur, and Silicon and the Related Elements, 120:1, 291-303
To link to this article: http://dx.doi.org/10.1080/10426509708545525
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