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Hexafluoroisopropanol as the Acid Component in the Passerini Reaction: One-Pot Access to ?-Amino Alcohols.

ABSTRACT: A new Passerini-type reaction in which hexafluoroisopropanol functions as the acid component is reported. The reaction tolerates a broad range of isocyanides and aldehydes, and the formed imidates can be reduced toward ?-amino alcohols under mild and metal-free conditions. In addition, the imidate products were shown to undergo an unprecedented retro-Passerini-type reaction under microwave conditions, providing valuable mechanistic information about the Passerini reaction and its variations.

SUBMITTER: Saya JM

PROVIDER: S-EPMC6038100 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Hexafluoroisopropanol as the Acid Component in the Passerini Reaction: One-Pot Access to β-Amino Alcohols.

Saya Jordy M JM Berabez Rayan R Broersen Pim P Schuringa Imme I Kruithof Art A Orru Romano V A RVA Ruijter Eelco E

Organic letters 20180615 13

A new Passerini-type reaction in which hexafluoroisopropanol functions as the acid component is reported. The reaction tolerates a broad range of isocyanides and aldehydes, and the formed imidates can be reduced toward β-amino alcohols under mild and metal-free conditions. In addition, the imidate products were shown to undergo an unprecedented retro-Passerini-type reaction under microwave conditions, providing valuable mechanistic information about the Passerini reaction and its variations. ...[more]

PMID: 29906122

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