A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives

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

doi:10.1016/S0040-4039(98)80042-7

A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives

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

Loughborough University

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

45 Citations (Scopus)

Abstract

A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper.

Original language	English
Pages (from-to)	143-146
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4039(98)80042-7
Publication status	Published - 1 Jan 1999

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title = "A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives",

abstract = "A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper.",

keywords = "Aminals, Amino alcohols, Diastereocontrol, Nitrogen heterocycles, Transition states",

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AU - Allin, Steven M.

AU - Northfield, Christopher J.

AU - Page, Michael I.

AU - Slawin, Alexandra M.Z.

PY - 1999/1/1

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N2 - A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper.

AB - A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper.

KW - Aminals

KW - Amino alcohols

KW - Diastereocontrol

KW - Nitrogen heterocycles

KW - Transition states

UR - https://www.scopus.com/pages/publications/0032890444

U2 - 10.1016/S0040-4039(98)80042-7

DO - 10.1016/S0040-4039(98)80042-7

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SP - 143

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives

Abstract

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