Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines
Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines
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DOI：
10.1021/jacs.5b03277
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发表时间：
2015-06-24
影响因子：
15
通讯作者：
Hayashi, Tamio
中科院分区：
文献类型：
--
作者：
Huang, Yinhua;Hayashi, Tamio
外消旋二芳基甲胺（（ArArCHNR 2）-Ar-1-C-1）（其中Ar-1被2-羟基取代）与芳基环硼氧烷（（ArBO）-B-3）（3）在手性二烯-铑催化剂存在下反应，得到高产率的手性三芳基甲烷（（ArArCH）-Ar-1-C-2*Ar-3），具有高的对映选择性（高达97%ee）。该反应被假定为进行通过邻醌甲基化物中间体进行铑催化的不对称1，4-加成的芳基硼试剂。
The reaction of racemic diarylmethylamines, ((ArArCHNR2)-Ar-1-C-1), where Ar-1 is substituted with a 2-hydroxy group, with arylboroxines ((ArBO)-B-3)(3) in the presence of a chiral diene-rhodium catalyst gave high yields of chiral triarylmethanes ((ArArCH)-Ar-1-C-2*Ar-3) with high enantioselectivity (up to 97% ee). The reaction is assumed to proceed through o-quinone methide intermediates which undergo Rh-catalyzed asymmetric 1,4-addition of the arylboron reagents.