Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines

被引：6

作者：

Nomura, Miku ^{[1
]}

Begum, Zubeda ^{[1
]}

Seki, Chigusa ^{[1
]}

Okuyama, Yuko ^{[1
,2
]}

Kwon, Eunsang ^{[3
]}

Uwai, Koji ^{[1
]}

Tokiwa, Michio ^{[4
]}

Tokiwa, Suguru ^{[4
]}

Takeshita, Mitsuhiro ^{[4
]}

Nakano, Hiroto ^{[1
]}

机构：

[1] Muroran Inst Technol, Grad Sch Engn, Div Sustainable & Environm Engn, 27-1 Mizumoto Cho, Muroran 0508585, Japan

[2] Tohoku Med & Pharmaceut Univ, 4-4-1 Komatsushima,Aoba Ku, Sendai 9818558, Japan

[3] Tohoku Med & Pharmaceut Univ, Res & Analyt Ctr Giant Mol, Grad Sch Sci, 4-4-1 Komatsushima,Aoba Ku, Sendai 9818558, Japan

[4] Tokiwakai Grp, 62 Numajiri Tsuduri Chou Uchigo, Iwaki 9738053, Japan

来源：

RSC ADVANCES | 2023年 / 13卷 / 06期

关键词：

MICHAEL ADDITION; N-BOC; ALDER REACTION; ESTERS; ALDOL; KETOESTERS; CATALYSIS; PROLINE; 1,3-DICARBONYLS; ALDEHYDES;

D O I：

10.1039/d2ra08317e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic functionality of new optically active thiourea fused gamma-amino alcohols was examined in the asymmetric Mannich reaction of beta-keto active methylene compounds with imines to afford chiral Mannich products, beta-amino keto compounds, with continuous chiral centers, that are versatile synthetic intermediates for deriving various biologically active compounds. In particular, the thiourea fused gamma-amino alcohols showed satisfactory catalytic activity in this reaction and afforded chiral Mannich products in excellent chemical yield (up to 88%) and stereoselectivities (up to syn : anti/93 : 7 dr, up to 99% ee).

引用

页码：3715 / 3722

页数：8

共 68 条

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