Please use this identifier to cite or link to this item: 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
Related resource: https://doi.org/10.1002/adsc.201600613
URI: http://hdl.handle.net/2445/106924
ISSN: 1615-4150
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

Files in This Item:
File Description SizeFormat 
667389.pdf1.08 MBAdobe PDFView/Open    Request a copy


Embargat   Document embargat fins el 28-2-2018


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.