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Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields

Financial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014-54306-P, CTQ2012-32436 and a RyC contract to A. L.) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931) are acknowledged

© Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853

Wiley

Author: Fernández Wang, Martí
Parera Briansó, Magda
Parella Coll, Teodor
Lledó Ponsati, Agustí
Le Bras, Jean
Muzart, Jacques
Pla i Quintana, Anna
Roglans i Ribas, Anna
Date: 2016 June 2
Abstract: A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields
Financial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014-54306-P, CTQ2012-32436 and a RyC contract to A. L.) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931) are acknowledged
Format: application/pdf
ISSN: 1615-4150 (versió paper)
1615-4169 (versió electrònica)
Document access: http://hdl.handle.net/10256/13146
Language: eng
Publisher: Wiley
Collection: MINECO/PE 2015-2017/CTQ2014-54306-P
AGAUR/2014-2016/2014 SGR-931
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/adsc.201600039
Articles publicats (D-Q)
Is part of: © Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853
Rights: Tots els drets reservats
Subject: Reaccions d’addició
Addition reactions
Catàlisi
Catalysis
Catalitzadors de rodi
Rhodium catalyst
Rodi
Rhodium
Title: Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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