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Enantioselective Synthesis of α‐ N ‐Alkylamino Acids via Sultam‐Directed ‘Enolate’ Hydroxyamination
Author(s) -
Oppolzer Wolfgang,
CintasMoreno Pedro,
Tamura Osamu,
Cardinaux Francis
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760113
Subject(s) - chemistry , hydrogenolysis , saponification , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis
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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