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trans ‐Tetrahydrofurans by OH‐Assisted Ru‐Catalyzed Isomerization of 2‐Butene‐1,4‐diols
Author(s) -
Fehr Charles,
Magpantay Iris,
Saudan Lionel,
Sommer Horst
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001166
Subject(s) - lactol , chemistry , isomerization , catalysis , lactone , medicinal chemistry , organic chemistry
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.