A Concise and Flexible Diastereoselective
Approach to Heteroring-Fused Isoindolinones

Gang Ahn; Magali Lorion; Vangelis Agouridas; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-0030-1258313

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Synthesis 2011(1): 147-153
DOI: 10.1055/s-0030-1258313

PAPER

A Concise and Flexible Diastereoselective Approach to Heteroring-Fused Isoindolinones

Gang Ahn^a,b, Magali Lorion^a,b, Vangelis Agouridas^a,b, Axel Couture*^a,c, Eric Deniau^a,b, Pierre Grandclaudon^a,b
^a Univ Lille Nord de France, 59000 Lille, France
Fax: +33(0)320436309; e-Mail: axel.couture@univ-lille1.fr;
^b USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), 59655 Villeneuve d’Ascq, France
^c CNRS, UMR 8181 ‘UCCS’, 59655 Villeneuve d’Ascq, France

Weitere Informationen

Publikationsverlauf

Received 7 September 2010
Publikationsdatum:
25. Oktober 2010 (online)

Abstract
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Abstract

A variety of poly and diversely substituted isoindolinones fused with six-membered heterocyclic moieties has been readily assembled through a sequence involving metalation of N-chloroalkylated models, subsequent interception with appropriate electrophiles and ultimate intramolecular annulation reaction.

Key words

carbanions - fused-ring systems - lactams - metalation - cyclization

References

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13

Selected X-ray crystallographic data for 9j: Empirical formula: C₁₉H₁₉NO₄; Mr = 325.35 g˙mol^-¹; F(000) = 688; white crystal; D = 1.353 g˙cm^-³; µ(Mo K_α) = 0.095; monoclinic; P21/n; a = 5.56820 (10) Å, b = 8.60050 (10) Å, c = 33.3710 (6) Å; α = 90.00, β = 91.8710 (10), γ = 90.00; V = 1597.26 (4) Å^³; Z = 4; T = 100 K. Further details of the X-ray structure data are available on request from the Cambridge Crystallographic Data Centre (CCDC 791641)