Asymmetric Synthesis using Sulfinimines (Thiooxime S-Oxides)

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.

KEYWORDS::

• Sulfinimines
• α-amino acids, N-sulfinylaziridine 2-carboxylic acids
• β-hydroxy-α-amino acids