Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes

被引：14

作者：

Schlinquer, Claire ^{[1
]}

Huang, Wei-Sheng ^{[1
]}

Chen, Ling ^{[1
]}

Poisson, Thomas ^{[1
,2
]}

Pannecoucke, Xavier ^{[1
]}

Charette, Andre B. ^{[3
]}

Jubault, Philippe ^{[1
]}

机构：

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

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

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 03期

关键词：

FUNCTIONALIZED MONOFLUORINATED CYCLOPROPANES; ASYMMETRIC CYCLOPROPANATION; ALLYLIC ALCOHOLS; AGONIST ACTIVITY; ACID-ANALOGS; FLUOROCYCLOPROPANATION; STRAIGHTFORWARD; FLUORINE; DESIGN; ACCESS;

D O I：

10.1039/c8ob03041c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric synthesis of mono-fluoro-, -chloro- and -bromomethyl-1,2-diaryl cyclopropane ester is described. The reaction, using Rh-2((S)-BTPCP)(4) as a catalyst, allowed the formation of the desired cyclopropanes in good to excellent yields (up to 99%) and excellent diastereoselectivities (up to >20:1) and with a high level of enantioselectivities (up to 98% ee). Finally, the synthetic utility of the chiral cyclopropanes was also demonstrated.

引用

页码：472 / 476

页数：5

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