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Gold‐Catalyzed Synthesis of Spirofused Indoloquinuclidines
Author(s) -
GlinskyOlivier Nicolas,
Retailleau Pascal,
Guinchard Xavier
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800357
Subject(s) - chemistry , tryptamine , catalysis , propargyl , phosphoric acid , pictet–spengler reaction , acetic acid , combinatorial chemistry , tandem , enantioselective synthesis , organic chemistry , stereochemistry , biochemistry , materials science , composite material
A novel series of spirofused indoloquinuclidines was obtained by a tandem Pictet–Spengler/Au I ‐catalyzed cyclization sequence. By combining N ‐propargyl tryptamine with aldehydes in the presence of acetic acid and a gold complex, the target indoloquinuclidines were obtained. The combination of a chiral phosphoric acid catalyst for the asymmetric Pictet–Spengler reaction with a gold complex furnished the target compounds with ee values up to 90 % in high diastereoselectivity.