An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles

Nicolas Duguet; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1021/ol901441t

An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles

Nicolas Duguet, Alexandra M. Z. Slawin, Andrew D. Smith

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

Abstract

The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

Original language	English
Pages (from-to)	3858-3861
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	17
DOIs	https://doi.org/10.1021/ol901441t
Publication status	Published - 3 Sept 2009

Keywords

INTRAMOLECULAR ALPHA-ARYLATION
QUATERNARY CARBON CENTERS
HECK REACTIONS
ENANTIOSELECTIVE SYNTHESIS
COPE REARRANGEMENT
OXINDOLE SYNTHESIS
NATURAL-PRODUCTS
CARBENE LIGANDS
DERIVATIVES
AMIDES

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title = "An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles",

abstract = "The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).",

keywords = "INTRAMOLECULAR ALPHA-ARYLATION, QUATERNARY CARBON CENTERS, HECK REACTIONS, ENANTIOSELECTIVE SYNTHESIS, COPE REARRANGEMENT, OXINDOLE SYNTHESIS, NATURAL-PRODUCTS, CARBENE LIGANDS, DERIVATIVES, AMIDES",

author = "Nicolas Duguet and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

year = "2009",

month = sep,

day = "3",

doi = "10.1021/ol901441t",

language = "English",

volume = "11",

pages = "3858--3861",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "17",

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TY - JOUR

T1 - An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles

AU - Duguet, Nicolas

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2009/9/3

Y1 - 2009/9/3

N2 - The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

AB - The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

KW - INTRAMOLECULAR ALPHA-ARYLATION

KW - QUATERNARY CARBON CENTERS

KW - HECK REACTIONS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - COPE REARRANGEMENT

KW - OXINDOLE SYNTHESIS

KW - NATURAL-PRODUCTS

KW - CARBENE LIGANDS

KW - DERIVATIVES

KW - AMIDES

U2 - 10.1021/ol901441t

DO - 10.1021/ol901441t

M3 - Article

SN - 1523-7060

VL - 11

SP - 3858

EP - 3861

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles

Abstract

Keywords

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