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Highly enantioselective addition of dimethylzinc to fluorinated alkyl ketones, and the mechanism behind it†
Chemical Communications ( IF 4.9 ) Pub Date : 2018-09-24 00:00:00 , DOI: 10.1039/c8cc06358c
Tomaz Neves-Garcia 1, 2, 3, 4, 5 , Andrea Vélez 1, 2, 3, 4, 5 , Jesús M. Martínez-Ilarduya 1, 2, 3, 4, 5 , Pablo Espinet 1, 2, 3, 4, 5
Affiliation  

Chiral-diamine catalyzed addition of ZnMe2 to PhC(O)CF2X (in dichloromethane at −30 °C) affords fluorinated alkyl tertiary alcohols in high yield (quantitative for X = H, F, Cl; 84% for X = CF3) and up to 99% ee. These conditions are similarly very efficient for other various ArC(O)CF3 molecules. A fine analysis of the results can be performed based on a double-cycle mechanism.

中文翻译:

将二甲基锌高度对映选择性地添加到氟化烷基酮中,以及其背后的机理

将手性二胺催化的ZnMe 2加到PhC(O)CF 2 X中(在-30°C的二氯甲烷中),可以得到高产率的氟化烷基叔醇(X = H,F,Cl定量; X = CF的定量为84%)3)和高达99%的ee。这些条件对于其他各种ArC(O)CF 3分子同样非常有效。可以基于双循环机制对结果进行精细分析。
更新日期:2018-09-24
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