PDF herunterladen
Synlett 1996; 1996(1): 43-45
DOI: 10.1055/s-1996-5332
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Highly Selective Ring-Cleavage of Acetals Catalyzed by Phenylboron Complexes Derived from Sulfonamides of α-Amino Acids

Motoharu Kinugasa, Toshiro Harada* , Katsuhiro Fujita, Akira Oku
  • *Department of Chemistry, Kyoto Institute of Technology, Sakyo-ku, Kyoto 606, Japan, Fax 75 724 7580
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

In the presence of catalytic amount of (0.1-0.5 equiv) of phenylboron complex 5d and nucleophiles 4a-e (1.5-1.1 equiv), chiral cyclic acetals (2S,4R)-3a-d undergo efficient ring-cleavage reaction to give 7a-h with high stereoselectivity. Removal of the chiral auxiliary from the ring-cleavage products 7a-h by a two step sequence furnishes functionalized secondary alcohols 8a-h of high enantiomeric purities.

acetal - diastereoselective ring-cleavage - Lewis acid catalyzed reaction - phenyl boron complex