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Synthesis 1989; 1989(12): 901-905
DOI: 10.1055/s-1989-27426
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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
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Publication Date:
02 May 2002 (online)

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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.

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