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

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

doi:10.1021/acscatal.8b03391

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

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

Science

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 language	English
Pages (from-to)	10392–10400
Number of pages	9
Journal	ACS Catalysis
Volume	8
Issue number	11
DOIs	https://doi.org/10.1021/acscatal.8b03391
Publication status	Published - 27 Sep 2018

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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

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title = "Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds",

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.",

keywords = "Chrial catalysts, bisoxazoline ligands, copper, cycloaddition, heterocycles, metal carbene",

author = "Kostiantyn Marichev and Adly, {Frady G.} and Alejandra Carranco and Estevan Garcia and Hadi Arman and Michael Doyle",

year = "2018",

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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

U2 - 10.1021/acscatal.8b03391

DO - 10.1021/acscatal.8b03391

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SP - 10392

EP - 10400

JO - ACS Catalysis

JF - ACS Catalysis

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