Catalytic Enantioselective Cyclopropanation of α-Fluoroacrylates: An Experimental and Theoretical Study

被引：30

作者：

Pons, Amandine ^{[1
]}

Tognetti, Vincent ^{[1
]}

Joubert, Laurent ^{[1
]}

Poisson, Thomas ^{[1
,2
]}

Pannecoucke, Xavier ^{[1
]}

Charette, Andre B. ^{[3
]}

Jubault, Philippe ^{[1
]}

机构：

[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA,UMR 6014, F-76000 Rouen, France

[2] Inst Univ France, 1 Rue Descartes, F-75231 Paris, France

[3] Univ Montreal, Ctr Green Chem & Catalysis, Fac Arts & Sci, Dept Chem, POB 6128,Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

ACS CATALYSIS | 2019年 / 9卷 / 03期

关键词：

fluorine; cyclopropanes; rhodium; DFT calculations; asymmetric synthesis; CYCLES; ACCESS; MODEL;

D O I：

10.1021/acscatal.9b00354

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Herein, we report the catalytic asymmetric synthesis of functionalized fluorocyclopropanes from alpha-fluoroacrylates. The method using Rh-2((S)-TCPTTL)(4) allowed the difficult reaction of an in situ-generated electrophilic Rh-carbene with an electron-poor alpha-fluoroacrylate. The desired fluorocyclopropanes were obtained in good yields, excellent dr and ee. Finally, the mechanism of this transformation was studied by density functional theory (DFT) calculations to explain the particular reactivity of the donor-acceptor diazo compounds with electron-deficient alpha-fluoroacrylates.

引用

页码：2594 / 2598

页数：9

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