Synthesis and structure of highly enantio- and diastereoenriched 1-aza-4-oxa-7-thiabicyclo[3.3.0]octan-8-ones derived from acyl-substituted S-benzyl thiocarbamates

Authors
Stratmann, O Hoppe, D Frohlich, R
Citation
O. Stratmann et al., Synthesis and structure of highly enantio- and diastereoenriched 1-aza-4-oxa-7-thiabicyclo[3.3.0]octan-8-ones derived from acyl-substituted S-benzyl thiocarbamates, J PRAK CHEM, 342(8), 2000, pp. 828-831
Citations number
10
Categorie Soggetti
Chemistry
Journal title
JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY
ISSN journal
14369966 → ACNP
Volume
342
Issue
8
Year of publication
2000
Pages
828 - 831
Database
ISI
SICI code
1436-9966(2000)342:8<828:SASOHE>2.0.ZU;2-B
Abstract
A convenient method for the synthesis of the title compounds 4a,b, 3a,b via an intramolecular condensation of thiourethanes, derived from the acylatio n of enantioenriched alpha -thio benzyllithium compounds, is reported. The structure of one of the major diastereomers was elucidated by a single-crys tal X-ray analysis and compared to semiempirical calculations.