2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for the enantioselective C-H functionalization of methyl ethers

David M. Guptill; Huw M.L. Davies

doi:10.1021/ja5107404

2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for the enantioselective C-H functionalization of methyl ethers

David M. Guptill, Huw M.L. Davies

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

100 Scopus citations

Abstract

A new class of reagents is described for C-H functionalization by means of C-H insertion using donor/acceptor-substituted rhodium(II) carbene intermediates. The 2,2,2-trichloroethyl aryl and heteroaryl diazoacetates, together with the dirhodium triarylcyclopropane carboxylate catalyst Rh₂(R-BPCP)₄, enabled the enantioselective intermolecular C-H functionalization of a range of methyl ethers with high levels of site selectivity and enantioselectivity.

Original language	English (US)
Pages (from-to)	17718-17721
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	51
DOIs	https://doi.org/10.1021/ja5107404
State	Published - Dec 24 2014

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© 2014 American Chemical Society.

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title = "2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for the enantioselective C-H functionalization of methyl ethers",

abstract = "A new class of reagents is described for C-H functionalization by means of C-H insertion using donor/acceptor-substituted rhodium(II) carbene intermediates. The 2,2,2-trichloroethyl aryl and heteroaryl diazoacetates, together with the dirhodium triarylcyclopropane carboxylate catalyst Rh2(R-BPCP)4, enabled the enantioselective intermolecular C-H functionalization of a range of methyl ethers with high levels of site selectivity and enantioselectivity.",

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T1 - 2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for the enantioselective C-H functionalization of methyl ethers

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AU - Davies, Huw M.L.

PY - 2014/12/24

Y1 - 2014/12/24

N2 - A new class of reagents is described for C-H functionalization by means of C-H insertion using donor/acceptor-substituted rhodium(II) carbene intermediates. The 2,2,2-trichloroethyl aryl and heteroaryl diazoacetates, together with the dirhodium triarylcyclopropane carboxylate catalyst Rh2(R-BPCP)4, enabled the enantioselective intermolecular C-H functionalization of a range of methyl ethers with high levels of site selectivity and enantioselectivity.

AB - A new class of reagents is described for C-H functionalization by means of C-H insertion using donor/acceptor-substituted rhodium(II) carbene intermediates. The 2,2,2-trichloroethyl aryl and heteroaryl diazoacetates, together with the dirhodium triarylcyclopropane carboxylate catalyst Rh2(R-BPCP)4, enabled the enantioselective intermolecular C-H functionalization of a range of methyl ethers with high levels of site selectivity and enantioselectivity.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 51

ER -

2,2,2-Trichloroethyl aryldiazoacetates as robust reagents for the enantioselective C-H functionalization of methyl ethers

Abstract

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