Design of Bronsted acid-assisted chiral Bronsted acid catalyst bearing a bis(triflyl) methyl group for a Mannich-type reaction

被引：127
|
作者：
Hasegawa, Aiko
Naganawa, Yuki
Fushimi, Makoto
Ishihara, Kazuaki
Yamamoto, Hisashi
机构：
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
[2] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 15期
关键词：
D O I：
10.1021/ol060939a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new Bronsted acid-assisted chiral Bronsted (chiral BBA) acid catalyst (1) was developed by substituting a hydroxy group of optically active 1,1'-bi(2-naphthol) with a stronger Bronsted acidic group such as a bis(trifluoromethanesulfonyl) methyl group. The enantioselective Mannich-type reaction of ketene silyl acetals with aldimines catalyzed by (R)-1 in the presence of stoichiometric achiral proton sources gave (S)-beta-amino esters in high yield with moderate to good enantiomeric excesses.
引用
收藏
页码：3175 / 3178
页数：4
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