Asymmetric Synthesis of α‐Amino Acids and α‐ N ‐Hydroxyamino Acids from  N ‐Acylbornane‐10,2‐sultams: 1‐chloro‐1‐nitrosocyclohexane as a practical [NH       2    +    ] equivalent | Zendy

Oppolzer Wolfgang | Zendy; Tamura Osamu | Zendy; Deerberg JöRg | Zendy

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Asymmetric Synthesis of α‐Amino Acids and α‐ N ‐Hydroxyamino Acids from N ‐Acylbornane‐10,2‐sultams: 1‐chloro‐1‐nitrosocyclohexane as a practical [NH 2 + ] equivalent

Author(s) -

Oppolzer Wolfgang,

Tamura Osamu,

Deerberg JöRg

Publication year - 1992

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.19920750622

Subject(s) - chemistry , reagent , amination , amino acid , sodium , isoleucine , medicinal chemistry , stereochemistry , organic chemistry , leucine , catalysis , biochemistry

Successive treatment of N ‐acylsultams 3 with sodium hexamethyldisilazide, 1‐chloro‐1‐nitrosocyclohexane ( 1 ), and aq. HCl gave diastereoisomerically pure, crystalline N ‐hydroxyamino‐acid derivatives 5 . These were converted into various amino acids 7 , N ‐hydroxyamino acids 8 , and an N ‐Boc‐amino acid 9 . ( S , S )‐Isoleucine ( 17 ) and ( S , S )‐2‐acetamido‐3‐phenylbutyric acid ( 23 ) were obtained from N ‐crotonoylsultam 15 via 1,4‐addition of an organomagnesium or organocopper reagent followed by enolate ‘amination’ with 1 .

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