175. Enantioselective Synthesis of α-N-Alkylamino Acidsvia Sultam-Directed ‘Enolate’ Hydroxyamination
     Oppolzer, W.; Cintas-Moreno, P.; Tamura, O.; Cardinaux, F.
     Helv. Chim. Acta 1993, 76, 187-196

Crystalline N-hydroxyamino-acid derivatives 4, readily available from non-chiral acyl chlorides 2 and sultams 1, were treated with aldehydes in the presence of NaBH₃CN to give N-alkylhydroxylamines 5. N,O-Hydrogenolysis of 5 and saponification of 6 furnished (S)-N-alkylamino acids 7 in high optical purity. Similarly, (R)-N-alkylamino acids 12 were obtained from the antipodal acylsultams 8.

DOI : 10.1002/hlca.19930760113 

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