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Studies on the chemistry and reactivity of alpha-substituted ketones in isonitrile-based multicomponent reactions.

ABSTRACT: Using the Passerini and Ugi reactions as representative tests, the utility of several alpha-substituted ketones R-CO-CH(2)-X (X = sulfonyloxy, acyloxy, azido, halo, hydroxy, and sulfonyl) in isonitrile-based multicomponent reactions was explored. In a relative rate study (R = PhCH(2)CH(2)), each of the alpha-substituted ketones underwent Passerini condensation more rapidly than the parent ketone. Short, highly convergent routes to oxazoline, beta-lactam, di-O-acylglyceramides, and other molecular frameworks were developed.

SUBMITTER: Fan L

PROVIDER: S-EPMC2736322 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Studies on the chemistry and reactivity of alpha-substituted ketones in isonitrile-based multicomponent reactions.

Fan Lijun L Adams Ashley M AM Polisar Jason G JG Ganem Bruce B

The Journal of organic chemistry 20081201 24

Using the Passerini and Ugi reactions as representative tests, the utility of several alpha-substituted ketones R-CO-CH(2)-X (X = sulfonyloxy, acyloxy, azido, halo, hydroxy, and sulfonyl) in isonitrile-based multicomponent reactions was explored. In a relative rate study (R = PhCH(2)CH(2)), each of the alpha-substituted ketones underwent Passerini condensation more rapidly than the parent ketone. Short, highly convergent routes to oxazoline, beta-lactam, di-O-acylglyceramides, and other molecula ...[more]

PMID: 18939871

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