From simple Ugi adducts to indanes and δ-amidomalonates: New manganese(III)-induced radical cascades

Laurent El Kaim; Laurence Grimaud; Emilie Vieu

doi:10.1021/ol701678d

From simple Ugi adducts to indanes and δ-amidomalonates: New manganese(III)-induced radical cascades

Laurent El Kaim
, Laurence Grimaud
, Emilie Vieu

Unité Chimie et Procédés

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

Abstract

A complete change of the traditional Ugi adducts framework has been obtained using new radical cascades as Ugi post-condensation reactions. Indanes and δ-amidomalonates were thus obtained in a one-pot procedure from aromatic aldehydes under a sequence involving Ugi addition followed by treatment of the adducts with Mn(III) and malonate or β-ketoester. The radical step probably involves an intramolecular aryl transfer followed by an oxidative cleavage and final cyclization to indanes.

Original language	English
Pages (from-to)	4171-4173
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	21
DOIs	https://doi.org/10.1021/ol701678d
Publication status	Published - 11 Oct 2007
Externally published	Yes

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title = "From simple Ugi adducts to indanes and δ-amidomalonates: New manganese(III)-induced radical cascades",

abstract = "A complete change of the traditional Ugi adducts framework has been obtained using new radical cascades as Ugi post-condensation reactions. Indanes and δ-amidomalonates were thus obtained in a one-pot procedure from aromatic aldehydes under a sequence involving Ugi addition followed by treatment of the adducts with Mn(III) and malonate or β-ketoester. The radical step probably involves an intramolecular aryl transfer followed by an oxidative cleavage and final cyclization to indanes.",

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doi = "10.1021/ol701678d",

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journal = "Organic Letters",

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T2 - New manganese(III)-induced radical cascades

AU - El Kaim, Laurent

AU - Grimaud, Laurence

AU - Vieu, Emilie

PY - 2007/10/11

Y1 - 2007/10/11

N2 - A complete change of the traditional Ugi adducts framework has been obtained using new radical cascades as Ugi post-condensation reactions. Indanes and δ-amidomalonates were thus obtained in a one-pot procedure from aromatic aldehydes under a sequence involving Ugi addition followed by treatment of the adducts with Mn(III) and malonate or β-ketoester. The radical step probably involves an intramolecular aryl transfer followed by an oxidative cleavage and final cyclization to indanes.

AB - A complete change of the traditional Ugi adducts framework has been obtained using new radical cascades as Ugi post-condensation reactions. Indanes and δ-amidomalonates were thus obtained in a one-pot procedure from aromatic aldehydes under a sequence involving Ugi addition followed by treatment of the adducts with Mn(III) and malonate or β-ketoester. The radical step probably involves an intramolecular aryl transfer followed by an oxidative cleavage and final cyclization to indanes.

U2 - 10.1021/ol701678d

DO - 10.1021/ol701678d

M3 - Article

AN - SCOPUS:35548941517

SN - 1523-7060

VL - 9

SP - 4171

EP - 4173

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

From simple Ugi adducts to indanes and δ-amidomalonates: New manganese(III)-induced radical cascades

Abstract

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