Promoting Thermodynamically Unfavorable [3,3] Rearrangements by Chemoselective Reduction

Promoting Thermodynamically Unfavorable [3,3] Rearrangements by Chemoselective Reduction

Herein described is a strategy for promoting thermodynamically unfavorable [3,3] Cope rearrangements. 3,3-Dicyano-1,5-dienes that are resistant to the thermal rearrangement can be promoted under reductive conditions. The reduced Cope products are versatile, bifunctional building blocks.

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Veröffentlicht in:Organic letters 2019-07, Vol.21 (14), p.5704-5707
Hauptverfasser: Vertesaljai, Peter, Serrano, Roberto, Mannchen, Michael D, Williams, Matthew, Semenova, Evgeniya, Grenning, Alexander J
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein described is a strategy for promoting thermodynamically unfavorable [3,3] Cope rearrangements. 3,3-Dicyano-1,5-dienes that are resistant to the thermal rearrangement can be promoted under reductive conditions. The reduced Cope products are versatile, bifunctional building blocks.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02057