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Synlett 1998; 1998(6): 668-670
DOI: 10.1055/s-1998-1730
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One Pot Synthesis of Cyclobutanols by Ring Expansion of Oxaspiropentanes Induced by Grignard Reagents

Angela M. Bernard* , Costantino Floris, Angelo Frongia, Pier P. Piras
  • *Dipartimento di Scienze Chimiche, Università di Cagliari, Via Ospedale 72, 09124 Cagliari (Italy); Fax (19)7 06 75 86 05; E-mail: pppiras@vaxca1.unica.it
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Publication History

Publication Date:
31 December 2000 (online)

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Aromatic, aliphatic and vinylic Grignard reagents efficiently catalyze the ring expansion of oxaspiropentanes 2 a,b to give, in one pot, good yields of cyclobutanols 3 a, 3 b - 7 b. Benzyl magnesium chloride gives a mixture of cyclobutanols and the cyclopropanol 8, probably coming from a direct nucleophilic attack on the epoxide part of the oxaspiropentane.

oxaspiropentanes - cyclobutanols - Grignard reagents - cyclopropanes - ring expansion