Rhodium-Catalyzed Cross-Aldol Reaction: In Situ Aldehyde-Enolate Formation from Allyloxyboranes and Primary Allylic Alcohols

Rhodium-Catalyzed Cross-Aldol Reaction: In Situ Aldehyde-Enolate Formation from Allyloxyboranes and Primary Allylic Alcohols

Dip in! A Rh/dippf catalyst generates aldehyde‐derived enol boranes at ambient temperature by isomerization of allyloxy‐ and homoallyloxyboranes. A one‐pot isomerization/cross‐aldol sequence provides aldehyde–aldehyde adducts in good yield with syn selectivity. Direct use of primary allylic and homo...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-10, Vol.51 (41), p.10275-10279
Hauptverfasser: Lin, Luqing, Yamamoto, Kumiko, Matsunaga, Shigeki, Kanai, Motomu
Format: Artikel
Sprache:eng
Schlagworte:
Adducts
Alcohols
Aldehydes - chemistry
aldol reaction
Ambient temperature
Boranes
Boranes - chemistry
boron
Catalysis
Catalysts
Dipping
Formations
homogeneous catalysis
Isomerization
Propanols - chemistry
Rhodium
Rhodium - chemistry
synthetic methods
transition metals
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Beschreibung
Zusammenfassung:Dip in! A Rh/dippf catalyst generates aldehyde‐derived enol boranes at ambient temperature by isomerization of allyloxy‐ and homoallyloxyboranes. A one‐pot isomerization/cross‐aldol sequence provides aldehyde–aldehyde adducts in good yield with syn selectivity. Direct use of primary allylic and homoallylic alcohols was also achieved.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201205680