PDF herunterladen
Synlett 1990; 1990(3): 169-170
DOI: 10.1055/s-1990-21025
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.

C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity

Simon R. Crabtree* , W. L. Alex Chu, Lewis N. Mander
  • *Research School of Chemistry, Australian National University, Canberra, A.C.T., 2601, Australia
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
08. März 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

The scope and limitations of the acylation of preformed lithium enolates by methyl cyanoformate have been explored further. In particular, the proportion of C-acylation products in sterically hindered substrates is significantly enhanced by the use of diethyl ether as solvent, while diastereofacial selectivity in the reactions of chiral enolates is found to be similar to that observed for C-alkylations in most cases. Exceptions may occur as a consequence of the higher steric demand of the cyanoformate reagent, however.