Download PDF
Synthesis 1989; 1989(12): 901-905
DOI: 10.1055/s-1989-27426
communication
© 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.

Vicinal Bromopropargoxylation of Cyclic Olefins and Cobaloxime-Mediated Heteroannulation to Functionalized 3-Methyleneoxacyclopentanes

Klaus Last* , H. M. R. Hoffmann
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-3000 Hannover, Federal Republic of Germany
Further Information

Publication History

Publication Date:
02 May 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The reaction of N-bromosuccinimide (NBS) and 2-propynol with cyclic olefins 1, including heteroaromatic benzofuran and N-protected indole, gave β-bromo-α-propargyl ethers 2. The adducts 2, some of which were quite sensitive, were cyclized with cobaloxime/sodium borohydride to give functionalized 3-methyleneoxacyclopentanes 3. The reaction sequence amounts to a simple two-step heteroannulation procedure.