Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

• Main Authors: Philipp Röse, Steffen Emge, Jun-ichi Yoshida, Gerhard Hilt
• Format: Article
• Language: English
• Published: Beilstein-Institut 2015-01-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: cyclic ethers; cyclisation; 1,4-dienes; electrochemistry; iodonium; selenium
• Online Access: https://doi.org/10.3762/bjoc.11.18
• ISSN: 1860-5397

The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.