Stereoconvergent ‘one-pot’ tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of acyclic bis-allylic ethers in the diastereoselective synthesis of substituted tetrahydropyrans

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Stereoconvergent ‘one-pot’ tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of acyclic bis-allylic ethers in the diastereoselective synthesis of substituted tetrahydropyrans

1994; Royal Society of Chemistry; Issue: 12 Linguagem: Inglês

10.1039/c39940001469

ISSN

2050-5639

Autores

Nick Greeves, K. J. VINES,

Tópico(s)

Chemical synthesis and alkaloids

Resumo

The unsaturated alcohols derived from a 'one-pot' tandem [2,3]-Wittig-anionic oxy-Cope (AOC) rearrangement undergo a halocyclisation reaction with iodine in acetonitrile to give substituted tetrahydropyrans with a high degree of stereocontrol.

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Stereoconvergent ‘one-pot’ tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of acyclic bis-allylic ethers in the diastereoselective synthesis of substituted tetrahydropyrans