Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives

Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives

Both enantiomers of 3‐hydroxyalkanoates and ‐alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)‐6‐methyl‐1,3‐oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α‐bromoamide is also discussed. Chirality 15:38–40,...

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Veröffentlicht in:Chirality (New York, N.Y.) N.Y.), 2003, Vol.15 (1), p.38-40
Hauptverfasser: Matsubara, Seijiro, Kasuga, Yuri, Yasui, Takuya, Yoshioka, Masahito, Yamin, Bohari, Utimoto, Kiitiro, Oshima, Koichiro
Format: Artikel
Sprache:eng
Schlagworte:
Acylation
aldol
Biological Factors - chemical synthesis
diastereoselective
enolate
Models, Molecular
Molecular Conformation
Oxathiins - chemistry
samarium
Stereoisomerism
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Zusammenfassung:Both enantiomers of 3‐hydroxyalkanoates and ‐alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)‐6‐methyl‐1,3‐oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α‐bromoamide is also discussed. Chirality 15:38–40, 2003. © 2002 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.10147