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

Research output: Contribution to journalArticle

21 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 languageEnglish
Pages (from-to)6332-6334
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number46
DOIs
Publication statusPublished - 2009

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