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Title: Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates
Author: Haraburda, Ewelina
Fernández, Martí
Gifreu, Anna
García Gómez, Jordi
Parella, Teodor
Pla-Quintana, Anna
Roglans i Ribas, Anna
Keywords: Rodi
Ciclització (Química)
Ring formation (Chemistry)
Issue Date: Feb-2017
Publisher: Wiley-VCH
Abstract: 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.
Note: Versió postprint del document publicat a:
It is part of: Advanced Synthesis & Catalysis, 2017, vol. 359, num. 3, p. 506-512
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ISSN: 1615-4150
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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