Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO2

被引：77

作者：

Takaishi, Kazuto ^{[1
,2
]}

Okuyama, Takafumi ^{[1
]}

Kadosaki, Shota ^{[1
]}

Uchiyama, Masanobu ^{[2
,3
]}

Ema, Tadashi ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Okayama 7008530, Japan

[2] RIKEN, Adv Elements Chem Lab, CPR, Wako, Saitama 3510198, Japan

[3] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

关键词：

MACROCYCLIC ORGANOCATALYSTS; ENANTIOSELECTIVE SYNTHESIS; CATALYZED CARBOXYLATION; SQUARAMIDE; CYCLOADDITION; DERIVATIVES; CONVERSION; AFFINITY; DIOXIDE; BINDING;

D O I：

10.1021/acs.orglett.9b00117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hemisquaramide tweezers, a new family of H-bond donor organocatalysts, are reported. The catalysts could be synthesized within two steps. Among them, H-8-binaphthyl-linked hemisquaramide 7 markedly accelerated the synthesis of cyclic carbonates from epoxides and CO2. The reactions proceeded well under mild and solvent-free conditions. Kinetic resolution was also achieved at -20 degrees C (s = 3.0). The adjustable bite angle and orientation of the two NH groups of the catalysts are important for the high activity.

引用

页码：1397 / 1401

页数：5

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