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Controlled heterocyclization/cross-coupling domino reaction of β,γ-allendiols and α-allenic esters: method and mechanistic insight for the preparation of functionalized buta-1,3-dienyl dihydropyrans.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2013 Oct 11; Vol. 19 (42), pp. 14233-44. Date of Electronic Publication: 2013 Aug 28. - Publication Year :
- 2013
-
Abstract
- Starting from β,γ-allendiols and α-allenic acetates, a chemo- and regiocontrolled palladium-catalyzed methodology has provided access to enantiopure 3,6-dihydropyrans that bear a buta-1,3-dienyl moiety. Thus, it has been demonstrated for the first time that the preparation of six-membered heterocycles through cross-coupling reactions of two different allenes can be accomplished. These heterocyclization/cross-coupling reactions have been developed experimentally and their mechanisms have additionally been investigated by a computational study.<br /> (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 19
- Issue :
- 42
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 24038421
- Full Text :
- https://doi.org/10.1002/chem.201300774