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Enantioselective Synthesis of α-N-Alkylamino Acids via Sultam-Directed ‘Enolate’ Hydroxyamination

✍ Scribed by Wolfgang Oppolzer; Pedro Cintas-Moreno; Osamu Tamura; Francis Cardinaux

Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
774 KB
Volume
76
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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 NaBH~3~CN 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.

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