AN ENANTIOSELECTIVE SYNTHESIS OF 2-IMIDAZOLIDINONES THROUGH BIFUNCTIONAL THIOUREA-CATALYZED TANDEM MANNICH/CYCLIZATION OF ISOCYANATOMALONATE DIESTER

被引：2
作者：
Kobayashi, Yusuke [1 ]
Yoshida, Takuma [1 ]
Uno, Takuya [1 ]
Tsukano, Chihiro [1 ]
Takemoto, Yoshiji [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
HETEROCYCLES | 2017年 / 95卷 / 02期
关键词：
Organocatalyst; Asymmetric Synthesis; MANNICH-TYPE REACTION; GLYCINE SCHIFF-BASES; CINCHONA ALKALOID THIOUREA; ALPHA-SUBSTITUTED NITROACETATES; CHIRAL AMMONIUM BETAINES; N-BOC-IMINES; ALPHA; BETA-DIAMINO ACIDS; ASYMMETRIC-SYNTHESIS; SYN-ALPHA; BIOLOGICAL SIGNIFICANCE;
D O I：
10.3987/COM-16-S(S)68
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral bifunctional thiourea-catalyzed Mannich reaction of diethyl 2-isocyanatomalonate with N-sulfonylimines was described. The tandem cyclization proceeded smoothly after Mannch reaction, directly furnishing chiral 2-imidazolidinones in 72-99% yields with 83-98% ees. Sterically demanding sulfonyl group was crucial for aliphatic imines to afford the corresponding product in high enantioselectivity.
引用
收藏
页码：980 / 993
页数：14
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