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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 .