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http://hdl.handle.net/2445/106924
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) Rhodium 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: https://doi.org/10.1002/adsc.201600613 |
It is part of: | Advanced Synthesis & Catalysis, 2017, vol. 359, num. 3, p. 506-512 |
URI: | http://hdl.handle.net/2445/106924 |
Related resource: | https://doi.org/10.1002/adsc.201600613 |
ISSN: | 1615-4150 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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