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trans-Tetrahydrofurans by OH-Assisted Ru-Catalyzed Isomerization of 2-Butene-1,4-diols

✍ Scribed by Charles Fehr; Iris Magpantay; Lionel Saudan; Horst Sommer

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 128 KB
Volume: 2010
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201001166

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✦ Synopsis

Abstract

We herein report a general method for the synthesis of 1,2‐annulated trans‐tetrahydrofurans by the OH‐assisted Ru‐catalyzed isomerization of (Z)‐2‐butene‐1,4‐diols (using Chaudret's catalyst), followed by reduction of the incipient lactol (using Et~3~SiH and Amberlyst 15). Alternatively, the lactol can be oxidized to the corresponding lactone (using Ikariya's catalyst). It was shown by labeling experiments that an addition/elimination pathway is (at least to some extent) operative for the isomerization reaction.

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