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