Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds

Kostiantyn Marichev, Frady G. Adly, Alejandra Carranco, Estevan Garcia, Hadi Arman, Michael Doyle

Research output: Contribution to journal › Article

12 Citations (Scopus)

Abstract

Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.
Original languageEnglish
Pages (from-to)10392–10400
Number of pages9
JournalACS Catalysis
Volume8
Issue number11
DOIs
Publication statusPublished - 27 Sep 2018

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Cycloaddition
Oxazines
Pyrazoles
Isoxazoles
Pyrazines
Stereoselectivity
Catalysts
Enantioselectivity
Amides
Copper
Esters
Derivatives
nitrones

Cite this

Marichev, K., Adly, F. G., Carranco, A., Garcia, E., Arman, H., & Doyle, M. (2018). Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds. ACS Catalysis, 8(11), 10392–10400. https://doi.org/10.1021/acscatal.8b03391
Marichev, Kostiantyn ; Adly, Frady G. ; Carranco, Alejandra ; Garcia, Estevan ; Arman, Hadi ; Doyle, Michael. / Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds. In: ACS Catalysis. 2018 ; Vol. 8, No. 11. pp. 10392–10400.
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abstract = "Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.",
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Marichev, K, Adly, FG, Carranco, A, Garcia, E, Arman, H & Doyle, M 2018, 'Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds', ACS Catalysis, vol. 8, no. 11, pp. 10392–10400. https://doi.org/10.1021/acscatal.8b03391

Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds. / Marichev, Kostiantyn; Adly, Frady G.; Carranco, Alejandra; Garcia, Estevan; Arman, Hadi; Doyle, Michael.

In: ACS Catalysis, Vol. 8, No. 11, 27.09.2018, p. 10392–10400.

Research output: Contribution to journal › Article

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T1 - Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds

AU - Marichev, Kostiantyn

AU - Adly, Frady G.

AU - Carranco, Alejandra

AU - Garcia, Estevan

AU - Arman, Hadi

AU - Doyle, Michael

PY - 2018/9/27

Y1 - 2018/9/27

N2 - Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.

AB - Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.

KW - Chrial catalysts

KW - bisoxazoline ligands

KW - copper

KW - cycloaddition

KW - heterocycles

KW - metal carbene

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DO - 10.1021/acscatal.8b03391

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JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

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Marichev K, Adly FG, Carranco A, Garcia E, Arman H, Doyle M. Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds. ACS Catalysis. 2018 Sep 27;8(11):10392–10400. https://doi.org/10.1021/acscatal.8b03391

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