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

Martí Fernández; Magda Parera; Teodor Parella; Agustí Lledó; Jean Le Bras; Jacques Muzart; Anna Pla-Quintana; Anna Roglans

doi:10.1002/adsc.201600039

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

Martí Fernández, Magda Parera, Teodor Parella, Agustí Lledó, Jean Le Bras, Jacques Muzart, Anna Pla-Quintana, Anna Roglans

Servei de Ressonància Magnètica Nuclear (SeRMN)

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Resum

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 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.

Idioma original	Anglès
Pàgines (de-a)	1848-1853
Revista	Advanced Synthesis and Catalysis
Volum	358
Número	11
DOIs	https://doi.org/10.1002/adsc.201600039
Estat de la publicació	Publicada - 1 de gen. 2016

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10.1002/adsc.201600039

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https://www.scopus.com/pages/publications/84971500174

CCDC 1429936: Experimental Crystal Structure Determination
Fernández, M. (Creador), Parera, M. (Creador), Parella, T. (Creador), Lledó, A. (Creador), Le Bras, J. (Creador), Muzart, J. (Creador), Pla-Quintana, A. (Creador) & Roglans, A. (Creador), Cambridge Crystallographic Data Centre, 6 d’oct. 2015
DOI: 10.5517/ccdc.csd.cc1jzyzf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1jzyzf&sid=DataCite
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Fernández, M., Parera, M., Parella, T., Lledó, A., Le Bras, J., Muzart, J., Pla-Quintana, A., & Roglans, A. (2016). Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds. Advanced Synthesis and Catalysis, 358(11), 1848-1853. https://doi.org/10.1002/adsc.201600039

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

abstract = "{\textcopyright} 2016 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim. 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.",

keywords = "cycloaddition, diastereoselectivity, kinetic resolution, Morita-Baylis-Hillman adducts, rhodium",

author = "Mart{\'i} Fern{\'a}ndez and Magda Parera and Teodor Parella and Agust{\'i} Lled{\'o} and \{Le Bras\}, Jean and Jacques Muzart and Anna Pla-Quintana and Anna Roglans",

year = "2016",

month = jan,

day = "1",

doi = "10.1002/adsc.201600039",

language = "English",

volume = "358",

pages = "1848--1853",

journal = "Advanced Synthesis and Catalysis",

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Fernández, M, Parera, M, Parella, T, Lledó, A, Le Bras, J, Muzart, J, Pla-Quintana, A & Roglans, A 2016, 'Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds', Advanced Synthesis and Catalysis, vol. 358, núm. 11, pàg. 1848-1853. https://doi.org/10.1002/adsc.201600039

Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds. / Fernández, Martí; Parera, Magda; Parella, Teodor et al.
In: Advanced Synthesis and Catalysis, Vol. 358, Núm. 11, 01.01.2016, pàg. 1848-1853.

Producció científica: Contribució a revista › Article › Recerca › Avaluat per experts

TY - JOUR

T1 - Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

AU - Fernández, Martí

AU - Parera, Magda

AU - Parella, Teodor

AU - Lledó, Agustí

AU - Le Bras, Jean

AU - Muzart, Jacques

AU - Pla-Quintana, Anna

AU - Roglans, Anna

PY - 2016/1/1

Y1 - 2016/1/1

N2 - © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 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.

AB - © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 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.

KW - cycloaddition

KW - diastereoselectivity

KW - kinetic resolution

KW - Morita-Baylis-Hillman adducts

KW - rhodium

UR - https://www.scopus.com/pages/publications/84971500174

U2 - 10.1002/adsc.201600039

DO - 10.1002/adsc.201600039

M3 - Article

SN - 1615-4150

VL - 358

SP - 1848

EP - 1853

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11

ER -

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

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CCDC 1429936: Experimental Crystal Structure Determination

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