Enantioselective Syntheses of α‐Amino Acids from 10‐(Aminosulfonyl)‐2‐bornyl Esters and Di( tert ‐butyl) Azodicarboxylate. Preliminary Communication | Zendy

Oppolzer Wolfgang | Zendy; Moretti Robert | Zendy

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Enantioselective Syntheses of α‐Amino Acids from 10‐(Aminosulfonyl)‐2‐bornyl Esters and Di( tert ‐butyl) Azodicarboxylate. Preliminary Communication

Author(s) -

Oppolzer Wolfgang,

Moretti Robert

Publication year - 1986

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.19860690819

Subject(s) - chemistry , enantioselective synthesis , hydrogenolysis , hydrolysis , diethyl azodicarboxylate , transesterification , enantiomer , organic chemistry , alcohol , amino acid , enantiomeric excess , catalysis , triphenylphosphine , biochemistry

Succesive treatment of chiral esters 1 with LiN(i‐Pr) 2 /Me 3 SiCl and di( tert ‐butyl) azodicarboxylate/TiCl 4 /Ti(i‐PrO) 4 gave N , N ′ ‐di[( tert ‐butoxy)carbonyl]hydrazino esters 9 which on deacylation, hydrogenolysis, transesterification, and acidic hydrolysis furnished (2 S )‐α‐amino acids 6 in high enantiomeric purity with efficient recovery of the auxiliary alcohol 7 .

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