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Gold‐Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration
Author(s) -
Milcendeau Pierre,
Gandon Vincent,
Guinchard Xavier
Publication year - 2021
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.202100007
Subject(s) - chemistry , intramolecular force , enamine , catalysis , group (periodic table) , functional group , medicinal chemistry , organic chemistry , stereochemistry , polymer
Tertiary amines bearing a benzyl‐type group (CH 2 Ar) undergo Au(I)‐catalyzed intramolecular addition to allenes. A formal 1,3‐transfer of the CH 2 Ar group takes place during the cyclization. As demonstrated by both experimental and DFT studies, these unprecedented intramolecular carboaminations involve two consecutive [3,3] rearrangements via a dearomatized intermediate. Because of the poor stability of the enamine products, protocols were developed to convert them in situ to more stable polycyclic chiral compounds.