Functionalised pyrrolidinones derived from (S)-pyroglutamic acid

Tetrahedron

Volumn 52, Issue 10, 1996, Pages 3719-3740

  Beard, Mark J ^a   Bailey, Jonathan H ^a   Cherry, David T ^a   Moloney, Mark G ^a   Shim, Sung Bo ^a   Statham, Kathryn A ^a   Bamford, Mark J ^b   Lamont, R Brian ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030066579     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00047-6     Document Type: Article

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41. Although the X-ray structural analysis confirmed the relative stereochemistry assigned by NMR spectroscopy, it also indicated that 3n was racemic, an entirely unexpected result given the non-zero optical rotation of the bulk sample. HPLC analysis indeed confirmed the racemic nature of the crystalline sample of 3n, but HPLC examination of the mother liquor demonstrated >99% optical purity. It was therefore concluded that the racemic crystals were formed by preferential crystallisation of the major enantiomer with the small amount of opposite enantiomer present, which arose from the starting (S)-pyroglutamic acid which was of 97% e.e.