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

Jordy M. Saya, Rayan Berabez, Pim Broersen, Imme Schuringa, Art Kruithof, Romano V.A. Orru, Eelco Ruijter

Research output: Contribution to JournalArticleAcademicpeer-review

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 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.

Original languageEnglish
Pages (from-to)3988-3991
Number of pages4
JournalOrganic Letters
Volume20
Issue number13
DOIs
Publication statusPublished - 6 Jul 2018

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Imidoesters
Amino Alcohols
alcohols
acids
Acids
Cyanides
Microwaves
Aldehydes
Metals
aldehydes
microwaves
hexafluoroisopropanol
products
metals

Cite this

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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 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.",
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Hexafluoroisopropanol as the Acid Component in the Passerini Reaction : One-Pot Access to β-Amino Alcohols. / Saya, Jordy M.; Berabez, Rayan; Broersen, Pim; Schuringa, Imme; Kruithof, Art; Orru, Romano V.A.; Ruijter, Eelco.

In: Organic Letters, Vol. 20, No. 13, 06.07.2018, p. 3988-3991.

Research output: Contribution to JournalArticleAcademicpeer-review

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T2 - One-Pot Access to β-Amino Alcohols

AU - Saya, Jordy M.

AU - Berabez, Rayan

AU - Broersen, Pim

AU - Schuringa, Imme

AU - Kruithof, Art

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

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