The enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over a cinchona alkaloid-modified palladium catalyst: Asymmetric synthesis of a cockroach attractant

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Abstract

A novel application of a cinchona-modified supported Pd catalyst is presented. The key step in the asymmetric synthesis of the cockroach attractant methyl (+)-tetrahydro-2H-pyran-3-carboxylate was the enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over 5% Pd/Al 2O3 modified by cinchonidine, which afforded the saturated product in up to 89% optical purity.

Original languageEnglish
Pages (from-to)1354-1358
Number of pages5
JournalNew Journal of Chemistry
Volume32
Issue number8
DOIs
Publication statusPublished - 2008

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Cinchona Alkaloids
Pyrans
Palladium
Carboxylic Acids
Carboxylic acids
Catalyst supports
Hydrogenation
Cinchona
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "A novel application of a cinchona-modified supported Pd catalyst is presented. The key step in the asymmetric synthesis of the cockroach attractant methyl (+)-tetrahydro-2H-pyran-3-carboxylate was the enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over 5{\%} Pd/Al 2O3 modified by cinchonidine, which afforded the saturated product in up to 89{\%} optical purity.",
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T1 - The enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over a cinchona alkaloid-modified palladium catalyst

T2 - Asymmetric synthesis of a cockroach attractant

AU - Szöri, K.

AU - Szöllősi, G.

AU - Bartók, M.

PY - 2008

Y1 - 2008

N2 - A novel application of a cinchona-modified supported Pd catalyst is presented. The key step in the asymmetric synthesis of the cockroach attractant methyl (+)-tetrahydro-2H-pyran-3-carboxylate was the enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over 5% Pd/Al 2O3 modified by cinchonidine, which afforded the saturated product in up to 89% optical purity.

AB - A novel application of a cinchona-modified supported Pd catalyst is presented. The key step in the asymmetric synthesis of the cockroach attractant methyl (+)-tetrahydro-2H-pyran-3-carboxylate was the enantioselective hydrogenation of 5,6-dihydro-2H-pyran-3-carboxylic acid over 5% Pd/Al 2O3 modified by cinchonidine, which afforded the saturated product in up to 89% optical purity.

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U2 - 10.1039/b808694j

DO - 10.1039/b808694j

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JO - New Journal of Chemistry

JF - New Journal of Chemistry

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