Oxidative cyclization of 1,4-dienes to yield 2,3,5-trisubstituted tetrahydrofuran-diols
2001; Elsevier BV; Volume: 42; Issue: 44 Linguagem: Inglês
10.1016/s0040-4039(01)01609-4
ISSN1873-3581
AutoresBenjamin R. Travis, Babak Borhan,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoKMnO4 and OsO4 catalyze the oxidative cyclization of 1,4-dienes to provide 2,3,5-trisubstituted tetrahydrofuran-diols in 30% yield. This reaction proceeds stereoselectively via a proposed [3+2] cycloaddition. Competing oxidative pathways are the major non-productive processes that reduce the yield of the reaction; however, four stereogenic centers are established in one-step.
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