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Mannich‐Type Reaction Using Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide
Author(s) -
Yanagisawa Akira,
Saito Hironao,
Harada Masanori,
Arai Takayoshi
Publication year - 2005
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.200505156
Subject(s) - chemistry , aldimine , catalysis , mannich reaction , methanol , organic chemistry , selectivity , reaction conditions , coupling reaction
A novel Mannich‐type reaction of alkenyl trichloroacetates with aldimines has been realized by using dibutyltin dimethoxide as a catalyst, which is regenerated by addition of methanol. A three‐component coupling reaction of aldehydes, primary amines, and alkenyl trichloroacetates has been also efficiently achieved. These procedures can provide a variety of β‐amino ketones not only from aromatic aldehydes but also from α,β‐unsaturated aldehydes mainly with syn ‐selectivity in high yields up to 99%.