Asymmetric Decarboxylative Allylation of Oxindoles

Vilius Franckevicius; James D. Cuthbertson; Mark Pickworth; David S. Pugh; Richard J. K. Taylor

doi:10.1021/ol201613a

Asymmetric Decarboxylative Allylation of Oxindoles

Vilius Franckevicius, James D. Cuthbertson, Mark Pickworth, David S. Pugh, Richard J. K. Taylor

Chemistry

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

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.

Original language	English
Pages (from-to)	4264-4267
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	16
DOIs	https://doi.org/10.1021/ol201613a
Publication status	Published - 19 Aug 2011

Keywords

ENANTIOSELECTIVE ALLYLIC ALKYLATION
PALLADIUM-CATALYZED ALLYLATION
QUATERNARY CARBON CENTERS
3-ALLYL-3-ARYL OXINDOLES
TSUJI ALLYLATION
ENOL CARBONATES
WORKING MODEL
C-H
KETONES
STEREOCENTERS

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10.1021/ol201613a

http://pubs.acs.org/doi/abs/10.1021/ol201613a

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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 = "ENANTIOSELECTIVE ALLYLIC ALKYLATION, PALLADIUM-CATALYZED ALLYLATION, QUATERNARY CARBON CENTERS, 3-ALLYL-3-ARYL OXINDOLES, TSUJI ALLYLATION, ENOL CARBONATES, WORKING MODEL, C-H, KETONES, STEREOCENTERS",

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",

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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 - ENANTIOSELECTIVE ALLYLIC ALKYLATION

KW - PALLADIUM-CATALYZED ALLYLATION

KW - QUATERNARY CARBON CENTERS

KW - 3-ALLYL-3-ARYL OXINDOLES

KW - TSUJI ALLYLATION

KW - ENOL CARBONATES

KW - WORKING MODEL

KW - C-H

KW - KETONES

KW - STEREOCENTERS

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U2 - 10.1021/ol201613a

DO - 10.1021/ol201613a

M3 - Article

SN - 1523-7060

VL - 13

SP - 4264

EP - 4267

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Asymmetric Decarboxylative Allylation of Oxindoles

Abstract

Keywords

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