Fitxers
Tipus de document
ArticleVersió
Versió acceptadaData de publicació
Tots els drets reservats
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/106924
Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates
Títol de la revista
Director/Tutor
ISSN de la revista
Títol del volum
Recurs relacionat
Resum
Allene-yne-allene and allene-ene-allene N-tosyl-linked substrates with two chiral centres in the α-position of the allene moiety were satisfactorily prepared starting both from racemic and chiral propargylic alcohols. The Wilkinson's complex-catalyzed [2+2+2] cycloaddition reaction of these substrates was evaluated. In the case of enantiomerically pure bisallenes, perfect stereoselectivity was observed, giving a diastereomerically pure cycloadduct. The chirality of starting bisallene substrates can be completely transferred to the cycloadducts, representing an atom-economical and enantiospecific process for the construction of fused polycycles. However, when reacting an oxygen-linked allene-ene-allene substrate, the stereoselectivity decreased and two diastereoisomers were formed. A detailed characterization study of the resulting cycloadducts allows us to identify the enantioisomer generated in the cycloaddition.
Matèries
Matèries (anglès)
Citació
Citació
HARABURDA, Ewelina, et al. Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates. Advanced Synthesis & Catalysis. 2017. Vol. 359, num. 3, pags. 506-512. ISSN 1615-4150. [consulted: 1 of June of 2026]. Available at: https://hdl.handle.net/2445/106924