Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

David A. Evans; Karl A. Scheidt; Keith R. Fandrick; Hon Wai Lam; Jimmy Wu

doi:10.1021/ja036985c

Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

David A. Evans^*, Karl A. Scheidt, Keith R. Fandrick, Hon Wai Lam, Jimmy Wu

^*Corresponding author for this work

Chemistry

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

241 Scopus citations

Abstract

A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves α,β-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture.

Original language	English (US)
Pages (from-to)	10780-10781
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	36
DOIs	https://doi.org/10.1021/ja036985c
State	Published - Sep 10 2003

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes",

abstract = "A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves α,β-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture.",

author = "Evans, {David A.} and Scheidt, {Karl A.} and Fandrick, {Keith R.} and Lam, {Hon Wai} and Jimmy Wu",

year = "2003",

month = sep,

day = "10",

doi = "10.1021/ja036985c",

language = "English (US)",

volume = "125",

pages = "10780--10781",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "36",

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T1 - Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

AU - Evans, David A.

AU - Scheidt, Karl A.

AU - Fandrick, Keith R.

AU - Lam, Hon Wai

AU - Wu, Jimmy

PY - 2003/9/10

Y1 - 2003/9/10

N2 - A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves α,β-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture.

AB - A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves α,β-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture.

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DO - 10.1021/ja036985c

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 36

ER -

Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

Abstract

ASJC Scopus subject areas

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