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A Gold‐Catalyzed A3 Coupling/Cyclization/Elimination Sequence as Versatile Tool for the Synthesis of Furfuryl Alcohol Derivatives from Glyceraldehyde and Alkynes
Author(s) -
Li Jian,
Rudolph Matthias,
Rominger Frank,
Xie Jin,
Hashmi. A. Stephen K.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500812
Subject(s) - chemistry , furfuryl alcohol , intramolecular force , morpholine , catalysis , combinatorial chemistry , aromatization , furan , glyceraldehyde , alcohol , intermolecular force , coupling reaction , organic chemistry , molecule , dehydrogenase , enzyme
The reaction of glyceraldehyde with alkynes delivers furfuryl alcohol derivatives within only one reaction step in the presence of a gold(III) catalyst. The reaction cascade is initiated by an intermolecular gold‐catalyzed A3 coupling sequence in which morpholine is used as additive. Intramolecular cyclization and subsequent aromatization under elimination of the amine then deliver the target molecules. The protocol offers a valuable alternative to the common routes that are based on functionalization of already existing furan cores.