Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands

Frady G. Adly, Kostiantyn Marichev, Joseph Jensen, Hadi Arman, Michael Doyle

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Enoldiazosulfones undergo [3 + 3]-cycloaddition with nitrones when catalyzed by copper(I) catalysts, but not with dirhodium(II) catalysts. Under mild reaction conditions with chiral bisoxazoline ligands, copper(I) catalysts produce 1,2-oxazine-sulfone derivatives in high yields and enantioselectivities. Dirhodium(II) catalysts form stable donor−acceptor cyclopropenes that undergo uncatalyzed [3 + 2]-cycloaddition reactions with nitrones.
Original languageEnglish
Pages (from-to)40-44
Number of pages5
JournalOrganic Letters
Volume21
Issue number1
DOIs
Publication statusPublished - 4 Jan 2019

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Cycloaddition
Cycloaddition Reaction
cycloaddition
Copper
Ligands
catalysts
copper
Sulfones
ligands
Catalysts
Oxazines
sulfones
Enantioselectivity
Derivatives
nitrones
oxazine 1

Cite this

Adly, Frady G. ; Marichev, Kostiantyn ; Jensen, Joseph ; Arman, Hadi ; Doyle, Michael. / Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands. In: Organic Letters. 2019 ; Vol. 21, No. 1. pp. 40-44.
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Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands. / Adly, Frady G.; Marichev, Kostiantyn; Jensen, Joseph; Arman, Hadi; Doyle, Michael.

In: Organic Letters, Vol. 21, No. 1, 04.01.2019, p. 40-44.

Research output: Contribution to journalArticle

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AU - Marichev, Kostiantyn

AU - Jensen, Joseph

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AU - Doyle, Michael

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