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An Efficient and Practical Method for the Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-02-08 , DOI: 10.1002/adsc.201701212
Lorenzo G. Borrego 1 , Rocío Recio 1 , Manuel Alcarranza 1 , Noureddine Khiar 2 , Inmaculada Fernández 1
Affiliation  

An efficient sulfinamide/olefin based chiral ligand, MetSulfolefin, has been developed for the enantioselective rhodium‐catalysed addition of aryl‐boronic acids to trifluoromethyl ketones. This shelf‐stable ligand is insensitive to air, oxygen and moisture, and it is obtained in only two high yielding steps from cheap commercially available (R)‐tert‐butanesulfinamide. The new ligand tolerates the use of hindered boronic acids and leads to the formation of a series of chiral trifluoromethyl‐substituted tertiary carbinols in high yields and excellent enantioselectivities (up to >99% ee).

中文翻译:

对映选择性合成叔三氟甲基甲醇的高效实用方法

已经开发出一种有效的基于亚磺酰胺/烯烃的手性配体MetSulf烯烃,用于对映体铑催化的芳基硼酸向三氟甲基酮的加成反应。这种耐贮存的配体对空气,氧气和湿气不敏感,仅需两个高收率的步骤即可从便宜的市售(R)-丁烷亚磺酰胺中获得。新的配体可耐受受阻硼酸的使用,并导致高收率和优异的对映选择性(高达> 99%ee)形成一系列手性三氟甲基取代的叔丁醇。
更新日期:2018-02-08
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