Synthesis of Indenes by Intramolecular
Morita-Baylis-Hillman Reaction in Aqueous Media
Catalyzed by Resin-Supported Proline

Kengo Akagawa; Seiji Sakamoto; Kazuaki Kudo

doi:10.1055/s-0030-1259683

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Synlett 2011(6): 817-820
DOI: 10.1055/s-0030-1259683

LETTER

Synthesis of Indenes by Intramolecular Morita-Baylis-Hillman Reaction in Aqueous Media Catalyzed by Resin-Supported Proline

Kengo Akagawa, Seiji Sakamoto, Kazuaki Kudo*
Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan
Fax: +81(3)54526359; e-Mail: kkudo@iis.u-tokyo.ac.jp;

Further Information

Publication History

Received 28 December 2010
Publication Date:
22 February 2011 (online)

Abstract
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References
Supplementary Material

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Abstract

Novel synthesis of indene derivatives has been developed in an organocatalytic way. Although homogeneous proline showed low catalytic efficiency, resin-supported proline effectively catalyzed the intramolecular Morita-Baylis-Hillman reaction to afford the desired indenes.

Key words

supported catalysis - annulation - aldehydes - proline - Morita-Baylis-Hillman reaction

Supporting Information

References and Notes

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14

TentaGel S-NH₂ (0.26 mmol/g amine loading, purchased from Fluka, product number: 86364) was used as a PEG-PS resin. Supported proline was prepared by the standard solid-phase peptide synthesis (ref. 7).

16

TentaGel S-NH₂ (0.45 mmol/g amine loading, purchased from Fluka, product number: 86359) was used for supporting proline.

Supplementary Material

Supporting Information