Parallel synthesis of tandem Ugi/Diels-Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

Masato Oikawa; Minoru Ikoma; Makoto Sasaki

doi:10.1016/j.tetlet.2004.11.115

Parallel synthesis of tandem Ugi/Diels-Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

Masato Oikawa, Minoru Ikoma, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Tohoku University

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

42 Citations (Scopus)

Abstract

A hundred reactions were demonstrated on the soluble MPEG-O-CH ₂-platform. The reaction can be also effected on insoluble TentaGel resin using the same linker. A series of parallel reactions were carried out for the tandem Ugi/Diels-Alder reaction on our MPEG-O-CH ₂- platform. Ninety-six out of a 100 entries were successful to give complex heterotricycles. The stereoselectivity was found not to be influenced by the building blocks used for amine and carboxylic acid components. An unexpected side pathway was found but was suppressed by employing appropriate reaction conditions. The reaction was also performed on solid phase, by which a larger library is potentially realized by employing the split-pool method.

Original language	English
Pages (from-to)	415-418
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.115
Publication status	Published - 2005 Jan 17

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10.1016/j.tetlet.2004.11.115

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Parallel synthesis of tandem Ugi/Diels-Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

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