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Vinylogous Mannich‐Type Reaction Catalyzed by an Iodine‐Substituted Chiral Phosphoric Acid
Author(s) -
Akiyama Takahiko,
Honma Yasuhiro,
Itoh Junji,
Fuchibe Kohei
Publication year - 2008
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.200700521
Subject(s) - chemistry , aldimine , phosphoric acid , mannich reaction , iodine , catalysis , brønsted–lowry acid–base theory , butenolide , organic chemistry , enantioselective synthesis
2‐Trimethylsiloxyfuran underwent a vinylogous Mannich‐type reaction with aldimines under the action of a new chiral phosphoric acid, bearing iodine on the 6,6′‐positions of the binaphthyl group, as a chiral Brønsted acid to give γ‐butenolide derivatives bearing an amino functionality with high diastereo‐ and enantioselectivity.