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*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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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.

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

Funding

The Netherlands Organization of Scientific Research (NWO) is acknowledged for financial support. We thank Elwin Janssen for technical assistance and NMR maintenance and Jurrien Collet for HRMS measurements (both Vrije Universiteit Amsterdam).

FundersFunder number
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

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