Title:
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Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates
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Author:
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Haraburda, Ewelina; Fernández, Martí; Gifreu, Anna; García Gómez, Jordi; Parella, Teodor; Pla-Quintana, Anna; Roglans i Ribas, Anna
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Other authors:
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Universitat de Barcelona |
Abstract:
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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. |
Subject(s):
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-Rodi -Ciclització (Química) -Rhodium -Ring formation (Chemistry) |
Rights:
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(c) Wiley-VCH, 2017
info:eu-repo/semantics/embargoedAccess |
Document type:
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Article Article - Accepted version |
Published by:
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Wiley-VCH
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