Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

Lianjin Zhang; Jin Bum Kim; Doo Ok Jang

doi:10.1016/j.tetlet.2014.03.023

Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

Lianjin Zhang, Jin Bum Kim, Doo Ok Jang

Chemistry and Medical Chemistry

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

13 Citations (Scopus)

Abstract

Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition-cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.

Original language	English
Pages (from-to)	2654-2658
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2014.03.023
Publication status	Published - 2014 Apr 16

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea ( NRF-2011-0021279 ).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.03.023

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title = "Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives",

abstract = "Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition-cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.",

author = "Lianjin Zhang and Kim, {Jin Bum} and Jang, {Doo Ok}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea ( NRF-2011-0021279 ).",

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doi = "10.1016/j.tetlet.2014.03.023",

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T1 - Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

AU - Zhang, Lianjin

AU - Kim, Jin Bum

AU - Jang, Doo Ok

N1 - Funding Information: This work was supported by the National Research Foundation of Korea ( NRF-2011-0021279 ).

PY - 2014/4/16

Y1 - 2014/4/16

N2 - Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition-cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.

AB - Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition-cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.

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DO - 10.1016/j.tetlet.2014.03.023

M3 - Article

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SN - 0040-4039

VL - 55

SP - 2654

EP - 2658

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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