ChemInform Abstract: Asymmetric Synthesis of Sulfinimines: Applications to the Synthesis of Nonracemic β-Amino Acids and α-Hydroxy β-Amino Acids.
Abstract
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ChemInform Abstract
Asymmetric oxidation of the sulfenimine (I) using a chiral oxaziridine produces the sulfinimine (II). This optically active ammonia synthon is coupled with the lithium enolate of methyl acetate (III). Subsequent chromatographic purification and acidic deprotection of (IV) gives the β-amino acid ester (VI). Furthermore, the enantiomer ( VII) of (IV) is converted to the N-benzoyl derivative (IX) which is subjected to oxidation with (+)-(camphorsulfonyl)oxaziridine to yield the α-hydroxy β-amino acid derivatives (X) and (XI).
