The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles

Mathilde Lachia; Cyril Poriel; Alexandra M. Z. Slawin; Christopher J. Moody

doi:10.1039/b613716d

The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles

Mathilde Lachia, Cyril Poriel, Alexandra M. Z. Slawin, Christopher J. Moody

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

20 Citations (Scopus)

Abstract

The nature of the 7-substituent has a remarkable effect on the diastereoselectivity of the oxidative rearrangement of indole-2-carboxamides derived from (S)-2-methoxymethylpyrrolidine into chiral 3,3-disubstituted oxindoles.

Original language	English
Pages (from-to)	286-288
Number of pages	3
Journal	Chemical Communications
Issue number	3
DOIs	https://doi.org/10.1039/b613716d
Publication status	Published - 2007

Keywords

QUATERNARY CARBON
DIAZONAMIDE-A
DIAZO ROUTE
CHLORINATION
ALKALOIDS
TRANSFORMATIONS
BENZOFURANONES
STEREOCENTERS
CONSTRUCTION
FRAGMENT

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10.1039/b613716d

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title = "The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles",

abstract = "The nature of the 7-substituent has a remarkable effect on the diastereoselectivity of the oxidative rearrangement of indole-2-carboxamides derived from (S)-2-methoxymethylpyrrolidine into chiral 3,3-disubstituted oxindoles.",

keywords = "QUATERNARY CARBON, DIAZONAMIDE-A, DIAZO ROUTE, CHLORINATION, ALKALOIDS, TRANSFORMATIONS, BENZOFURANONES, STEREOCENTERS, CONSTRUCTION, FRAGMENT",

author = "Mathilde Lachia and Cyril Poriel and Slawin, {Alexandra M. Z.} and Moody, {Christopher J.}",

year = "2007",

doi = "10.1039/b613716d",

language = "English",

pages = "286--288",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "3",

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T1 - The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles

AU - Lachia, Mathilde

AU - Poriel, Cyril

AU - Slawin, Alexandra M. Z.

AU - Moody, Christopher J.

PY - 2007

Y1 - 2007

N2 - The nature of the 7-substituent has a remarkable effect on the diastereoselectivity of the oxidative rearrangement of indole-2-carboxamides derived from (S)-2-methoxymethylpyrrolidine into chiral 3,3-disubstituted oxindoles.

AB - The nature of the 7-substituent has a remarkable effect on the diastereoselectivity of the oxidative rearrangement of indole-2-carboxamides derived from (S)-2-methoxymethylpyrrolidine into chiral 3,3-disubstituted oxindoles.

KW - QUATERNARY CARBON

KW - DIAZONAMIDE-A

KW - DIAZO ROUTE

KW - CHLORINATION

KW - ALKALOIDS

KW - TRANSFORMATIONS

KW - BENZOFURANONES

KW - STEREOCENTERS

KW - CONSTRUCTION

KW - FRAGMENT

UR - http://www.scopus.com/inward/record.url?scp=33845997417&partnerID=8YFLogxK

U2 - 10.1039/b613716d

DO - 10.1039/b613716d

M3 - Article

SN - 1359-7345

SP - 286

EP - 288

JO - Chemical Communications

JF - Chemical Communications

IS - 3

ER -

The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles

Abstract

Keywords

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