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

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 p...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 20; no. 13; pp. 3988 - 3991
Main Authors Saya, Jordy M, Berabez, Rayan, Broersen, Pim, Schuringa, Imme, Kruithof, Art, Orru, Romano V. A, Ruijter, Eelco
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
MULTICOMPONENT REACTIONS
ORGANIC-SYNTHESIS
ISOCYANIDES
COMPLEXITY
CHEMISTRY
COUPLINGS
DERIVATIVES TOTAL-SYNTHESIS
DIVERSE HETEROCYCLIC SCAFFOLDS
EFFICIENCY
TRANSFORMATIONS
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01561