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

Jordy M. Saya | Zendy; Rayan Berabez | Zendy; Pim Broersen | Zendy; Imme Schuringa | Zendy; Art Kruithof | Zendy; Romano V. A. Orrù | Zendy; Eelco Ruijter | Zendy

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

Author(s) -

Jordy M. Saya,

Rayan Berabez,

Pim Broersen,

Imme Schuringa,

Art Kruithof,

Romano V. A. Orrù,

Eelco Ruijter

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b01561

Subject(s) - chemistry , component (thermodynamics) , reaction conditions , organic chemistry , amino acid , combinatorial chemistry , catalysis , primary (astronomy) , biochemistry , physics , astronomy , thermodynamics

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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