Abstract
The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.
Original language | English (US) |
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Pages (from-to) | 14006-14011 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 138 |
Issue number | 42 |
DOIs | |
State | Published - Oct 26 2016 |
Bibliographical note
Publisher Copyright:© 2016 American Chemical Society.