Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

Steven M. Allin; Christopher J. Northfield; Michael I. Page; Alexandra M.Z. Slawin

doi:10.1039/b001569p

Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

Steven M. Allin, Christopher J. Northfield, Michael I. Page, Alexandra M.Z. Slawin

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

58 Citations (Scopus)

Abstract

New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol derived chiral auxiliary can be achieved without loss of stereochemical integrity at the newly created asymmetric centre, and we report a novel method for this key step using conc. sulfuric acid.

Original language	English
Pages (from-to)	1715-1721
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	11
DOIs	https://doi.org/10.1039/b001569p
Publication status	Published - 2000

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abstract = "New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol derived chiral auxiliary can be achieved without loss of stereochemical integrity at the newly created asymmetric centre, and we report a novel method for this key step using conc. sulfuric acid.",

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AU - Northfield, Christopher J.

AU - Page, Michael I.

AU - Slawin, Alexandra M.Z.

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AB - New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol derived chiral auxiliary can be achieved without loss of stereochemical integrity at the newly created asymmetric centre, and we report a novel method for this key step using conc. sulfuric acid.

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ER -

Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

Abstract

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