Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

M. Paravidino; R.S. Bon; R. Scheffelaar; D.J. Vugts; A. Znabet; R.F. Schmitz; F.J.J. de Kanter; M. Lutz; A.L Spek; M.B. Groen; R.V.A. Orru

doi:10.1021/ol062204b

Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

M. Paravidino
, R.S. Bon
, R. Scheffelaar
, D.J. Vugts
, A. Znabet
, R.F. Schmitz
, F.J.J. de Kanter
, M. Lutz
, A.L Spek
, M.B. Groen
, R.V.A. Orru

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	5369-72
Journal	Organic letters
Volume	8
Issue number	23
DOIs	https://doi.org/10.1021/ol062204b
Publication status	Published - 2006

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10.1021/ol062204b

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CCDC 612759: Experimental Crystal Structure Determination
Paravidino, M. (Contributor), Bon, R. S. (Contributor), Scheffelaar, R. (Contributor), Vugts, D. J. (Contributor), Znabet, A. (Contributor), Schmitz, R. F. (Contributor), De Kanter, F. J. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Groen, M. B. (Contributor) & Orru, R. V. A. (Contributor), Unknown, 1 Jan 2007
DOI: 10.5517/ccnkmf7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnkmf7&sid=DataCite
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title = "Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality",

abstract = "In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation. {\textcopyright} 2006 American Chemical Society.",

author = "M. Paravidino and R.S. Bon and R. Scheffelaar and D.J. Vugts and A. Znabet and R.F. Schmitz and \{de Kanter\}, F.J.J. and M. Lutz and A.L Spek and M.B. Groen and R.V.A. Orru",

year = "2006",

doi = "10.1021/ol062204b",

language = "English",

volume = "8",

pages = "5369--72",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

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TY - JOUR

T1 - Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

AU - Paravidino, M.

AU - Bon, R.S.

AU - Scheffelaar, R.

AU - Vugts, D.J.

AU - Znabet, A.

AU - Schmitz, R.F.

AU - de Kanter, F.J.J.

AU - Lutz, M.

AU - Spek, A.L

AU - Groen, M.B.

AU - Orru, R.V.A.

PY - 2006

Y1 - 2006

N2 - In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation. © 2006 American Chemical Society.

AB - In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation. © 2006 American Chemical Society.

U2 - 10.1021/ol062204b

DO - 10.1021/ol062204b

M3 - Article

SN - 1523-7060

VL - 8

SP - 5369

EP - 5372

JO - Organic letters

JF - Organic letters

IS - 23

ER -

Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

Abstract

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CCDC 612759: Experimental Crystal Structure Determination

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