RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
PDF herunterladen
Synfacts 2022; 18(03): 0271
DOI: 10.1055/s-0041-1737854
DOI: 10.1055/s-0041-1737854
Metals in Synthesis
Access to Oxazaborolidines by Catalytic Cycloaddition of 1,2-Azaborines and Vinyl Ethylene Carbonate
Autoren
Morita T,
Murakami H,
Asawa Y,
Nakamura H.
*
Tokyo Institute of Technology, Yokohama, Japan
Enantioselective Synthesis of Oxazaborolidines by Palladium-Catalyzed N−H/B−H Double Activation of 1,2-Azaborines.
Angew. Chem. Int. Ed. 2022;
61
DOI: 10.1002/anie.202113558
Enantioselective Synthesis of Oxazaborolidines by Palladium-Catalyzed N−H/B−H Double Activation of 1,2-Azaborines.
Angew. Chem. Int. Ed. 2022;
61
DOI: 10.1002/anie.202113558
Key words
asymmetric synthesis - 1,2-azaborines - cycloaddition - oxazaborolidines - palladium catalysis - vinylethylene carbonates
Significance
A palladium-catalyzed protocol for the (asymmetric) construction of oxazaborolidines is reported. The transformation proceeds through a decarboxylative/dehydrogenative (3+2) cycloaddition of 1,2-azaborines and vinyl ethylene carbonate.
Comment
This procedure provides access to polycyclic oxazaborolidines in good yields and excellent enantioselectivities. Mechanistic experiments support the release of molecular H2 from the zwitterionic intermediate A.
Publikationsverlauf
Artikel online veröffentlicht:
16. Februar 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany