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Asymmetric Decarboxylative Allylation of Oxindoles

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Asymmetric Decarboxylative Allylation of Oxindoles. / Franckevicius, Vilius; Cuthbertson, James D.; Pickworth, Mark et al.
In: Organic Letters, Vol. 13, No. 16, 19.08.2011, p. 4264-4267.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Franckevicius, V, Cuthbertson, JD, Pickworth, M, Pugh, DS & Taylor, RJK 2011, 'Asymmetric Decarboxylative Allylation of Oxindoles', Organic Letters, vol. 13, no. 16, pp. 4264-4267. https://doi.org/10.1021/ol201613a

APA

Franckevicius, V., Cuthbertson, J. D., Pickworth, M., Pugh, D. S., & Taylor, R. J. K. (2011). Asymmetric Decarboxylative Allylation of Oxindoles. Organic Letters, 13(16), 4264-4267. https://doi.org/10.1021/ol201613a

Vancouver

Franckevicius V, Cuthbertson JD, Pickworth M, Pugh DS, Taylor RJK. Asymmetric Decarboxylative Allylation of Oxindoles. Organic Letters. 2011 Aug 19;13(16):4264-4267. doi: 10.1021/ol201613a

Author

Franckevicius, Vilius ; Cuthbertson, James D. ; Pickworth, Mark et al. / Asymmetric Decarboxylative Allylation of Oxindoles. In: Organic Letters. 2011 ; Vol. 13, No. 16. pp. 4264-4267.

Bibtex

@article{9adbcc3d0e4c4124ba3a8a675dec1fdc,
title = "Asymmetric Decarboxylative Allylation of Oxindoles",
abstract = "An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.",
keywords = "STEREOCENTERS, PALLADIUM-CATALYZED ALLYLATION, QUATERNARY CARBON CENTERS, WORKING MODEL, KETONES, ENOL CARBONATES, 3-ALLYL-3-ARYL OXINDOLES, ENANTIOSELECTIVE ALLYLIC ALKYLATION, TSUJI ALLYLATION, C-H",
author = "Vilius Franckevicius and Cuthbertson, {James D.} and Mark Pickworth and Pugh, {David S.} and Taylor, {Richard J. K.}",
year = "2011",
month = aug,
day = "19",
doi = "10.1021/ol201613a",
language = "English",
volume = "13",
pages = "4264--4267",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "16",

}

RIS

TY - JOUR

T1 - Asymmetric Decarboxylative Allylation of Oxindoles

AU - Franckevicius, Vilius

AU - Cuthbertson, James D.

AU - Pickworth, Mark

AU - Pugh, David S.

AU - Taylor, Richard J. K.

PY - 2011/8/19

Y1 - 2011/8/19

N2 - An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

AB - An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

KW - STEREOCENTERS

KW - PALLADIUM-CATALYZED ALLYLATION

KW - QUATERNARY CARBON CENTERS

KW - WORKING MODEL

KW - KETONES

KW - ENOL CARBONATES

KW - 3-ALLYL-3-ARYL OXINDOLES

KW - ENANTIOSELECTIVE ALLYLIC ALKYLATION

KW - TSUJI ALLYLATION

KW - C-H

UR - http://www.scopus.com/inward/record.url?scp=80051699882&partnerID=8YFLogxK

U2 - 10.1021/ol201613a

DO - 10.1021/ol201613a

M3 - Journal article

VL - 13

SP - 4264

EP - 4267

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 16

ER -