A novel and highly stereoselective route for the synthesis of non-racemic 3-substituted isoindolin-1-one targets

Ryan A. Hemming; Megan Bell; Liam J. Duffy; Jonathan Bristow; John D. Wallis; Steven M. Allin; Philip C. Bulman Page

doi:10.1016/j.tet.2018.11.050

A novel and highly stereoselective route for the synthesis of non-racemic 3-substituted isoindolin-1-one targets

Ryan A. Hemming, Megan Bell, Liam J. Duffy, Jonathan Bristow, John D. Wallis, Steven M. Allin, Philip C. Bulman Page

Chemistry of Materials and Catalysis

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Abstract

A new, versatile and highly stereoselective approach for the synthesis of non-racemic 3-substituted isoindolin-1-ones is described from a readily available chiral template. The potential of this new protocol is demonstrated through the synthesis of an enantiomerically enriched 3-alkyl N-H isoindolin-1-one target with an e.e. of 98%.

Original language	English
Pages (from-to)	121-127
Number of pages	7
Journal	Tetrahedron
Volume	75
Issue number	1
Early online date	24 Nov 2018
DOIs	https://doi.org/10.1016/j.tet.2018.11.050
Publication status	Published - 3 Jan 2019

Keywords

Isoindolinone
N-Acyliminium
Stereoselective synthesis

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10.1016/j.tet.2018.11.050

AAM_Tetrahedron_Hemming_etalAccepted author manuscript, 683 KBLicence: CC BY-NC-ND

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abstract = "A new, versatile and highly stereoselective approach for the synthesis of non-racemic 3-substituted isoindolin-1-ones is described from a readily available chiral template. The potential of this new protocol is demonstrated through the synthesis of an enantiomerically enriched 3-alkyl N-H isoindolin-1-one target with an e.e. of 98%.",

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AU - Hemming, Ryan A.

AU - Bell, Megan

AU - Duffy, Liam J.

AU - Bristow, Jonathan

AU - Wallis, John D.

AU - Allin, Steven M.

AU - Bulman Page, Philip C.

PY - 2019/1/3

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AB - A new, versatile and highly stereoselective approach for the synthesis of non-racemic 3-substituted isoindolin-1-ones is described from a readily available chiral template. The potential of this new protocol is demonstrated through the synthesis of an enantiomerically enriched 3-alkyl N-H isoindolin-1-one target with an e.e. of 98%.

KW - Isoindolinone

KW - N-Acyliminium

KW - Stereoselective synthesis

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DO - 10.1016/j.tet.2018.11.050

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JF - Tetrahedron

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ER -

A novel and highly stereoselective route for the synthesis of non-racemic 3-substituted isoindolin-1-one targets

Abstract

Keywords

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