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

SM Allin; CJ Northfield; MI Page; Alexandra Martha Zoya Slawin

doi:10.1039/b001569p

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

SM Allin, CJ Northfield, MI Page, Alexandra Martha Zoya Slawin

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

Abstract

New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

HIGHLY DIASTEREOSELECTIVE SYNTHESIS
ENANTIOSELECTIVE TOTAL SYNTHESES
HIV-1 REVERSE-TRANSCRIPTASE
SIMPLE ASYMMETRIC-SYNTHESIS
2-SUBSTITUTED PYRROLIDINES
PRECURSORS
INHIBITORS
LACTAMS

Access to Document

10.1039/b001569p

Cite this

@article{a755dc8ac2a9444dad7d113c9719dbdc,

title = "Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives",

abstract = "New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-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.",

keywords = "HIGHLY DIASTEREOSELECTIVE SYNTHESIS, ENANTIOSELECTIVE TOTAL SYNTHESES, HIV-1 REVERSE-TRANSCRIPTASE, SIMPLE ASYMMETRIC-SYNTHESIS, 2-SUBSTITUTED PYRROLIDINES, PRECURSORS, INHIBITORS, LACTAMS",

author = "SM Allin and CJ Northfield and MI Page and Slawin, \{Alexandra Martha Zoya\}",

year = "2000",

doi = "10.1039/b001569p",

language = "English",

pages = "1715--1721",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Chemical Society",

number = "11",

}

TY - JOUR

T1 - Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

AU - Allin, SM

AU - Northfield, CJ

AU - Page, MI

AU - Slawin, Alexandra Martha Zoya

PY - 2000

Y1 - 2000

N2 - New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-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.

AB - New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-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.

KW - HIGHLY DIASTEREOSELECTIVE SYNTHESIS

KW - ENANTIOSELECTIVE TOTAL SYNTHESES

KW - HIV-1 REVERSE-TRANSCRIPTASE

KW - SIMPLE ASYMMETRIC-SYNTHESIS

KW - 2-SUBSTITUTED PYRROLIDINES

KW - PRECURSORS

KW - INHIBITORS

KW - LACTAMS

UR - https://www.scopus.com/pages/publications/0034616722

U2 - 10.1039/b001569p

DO - 10.1039/b001569p

M3 - Article

SN - 1470-4358

SP - 1715

EP - 1721

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 11

ER -

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

Abstract

UN SDGs

Keywords

Access to Document

Other files and links

Fingerprint

Cite this