Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement

Muhammad Ismail; Huy V. Nguyen; Gennadiy Ilyashenko; Majid Motevalli; Christopher J. Richards

doi:10.1016/j.tetlet.2009.08.122

Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement

Muhammad Ismail, Huy V. Nguyen, Gennadiy Ilyashenko, Majid Motevalli, Christopher J. Richards

Chemistry of Materials and Catalysis

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

23 Citations (Scopus)

Abstract

A catalysed O/C-carboxyl rearrangement generates the all-carbon stereogenic centre in phenyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate (up to 57% ee). Crystallisation and removal of racemic crystals enhance the ee to 95%. The X-ray crystal structure of the cobalt metallocene-pyrrolidinopyridine nucleophilic catalyst employed is reported. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6332-6334
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2009.08.122
Publication status	Published - 2009

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10.1016/j.tetlet.2009.08.122

Cite this

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title = "Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement",

abstract = "A catalysed O/C-carboxyl rearrangement generates the all-carbon stereogenic centre in phenyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate (up to 57% ee). Crystallisation and removal of racemic crystals enhance the ee to 95%. The X-ray crystal structure of the cobalt metallocene-pyrrolidinopyridine nucleophilic catalyst employed is reported. (C) 2009 Elsevier Ltd. All rights reserved.",

author = "Muhammad Ismail and Nguyen, {Huy V.} and Gennadiy Ilyashenko and Majid Motevalli and Richards, {Christopher J.}",

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AU - Motevalli, Majid

AU - Richards, Christopher J.

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AB - A catalysed O/C-carboxyl rearrangement generates the all-carbon stereogenic centre in phenyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate (up to 57% ee). Crystallisation and removal of racemic crystals enhance the ee to 95%. The X-ray crystal structure of the cobalt metallocene-pyrrolidinopyridine nucleophilic catalyst employed is reported. (C) 2009 Elsevier Ltd. All rights reserved.

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DO - 10.1016/j.tetlet.2009.08.122

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