The β-silicon effect as a control element for the regioselective ring opening of oxetanes

Thorsten Bach, Kristian Kather

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The title compounds 5 was prepared by a stereoselective photocycloaddition of silyl enol ether 9 and benzaldehyde. In Lewis- and Brönsted-acid promoted ring opening reactions the oxetane is selectively cleaved to yield a 1,2-diol 6 which cyclizes under the reaction conditions to the dihydrofuran 11. The constitution of the final product was elucidated by reductive to the alcohol 14.

Original languageEnglish
Pages (from-to)12319-12328
Number of pages10
JournalTetrahedron
Volume50
Issue number43
DOIs
StatePublished - 1994
Externally publishedYes

Fingerprint

Dive into the research topics of 'The β-silicon effect as a control element for the regioselective ring opening of oxetanes'. Together they form a unique fingerprint.

Cite this