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Pd-Catalyzed Dimethylation of Tyrosine-Derived Picolinamide for Synthesis of (S)-N-Boc-2,6-dimethyltyrosine and Its Analogues
Organic Letters ( IF 4.9 ) Pub Date : 2016-12-27 00:00:00 , DOI: 10.1021/acs.orglett.6b03548
Xuning Wang 1 , Songtao Niu 1 , Lanting Xu 2 , Chao Zhang 2 , Lingxing Meng 2 , Xiaojing Zhang 1 , Dawei Ma 2
Affiliation  

A short and efficient synthesis of (S)-N-Boc-2,6-dimethyltyrosine utilizing palladium-catalyzed directed C–H functionalization is described. This represents the first general method for the ortho-dimethylation of tyrosine derivatives and offers a practical approach for preparing this synthetically important building block. Notably, throughout the reaction sequence no racemization occurs at the susceptible α-chiral centers.

中文翻译:

Pd催化酪氨酸衍生的吡啶啉二甲基化反应合成(S-N -Boc-2,6-二甲基酪氨酸及其类似物

描述了利用钯催化的直接CH官能团的短而有效的合成(S-N -Boc-2,6-二甲基酪氨酸的方法。这代表了酪氨酸衍生物的二甲基化的第一种通用方法,并为制备这种具有重要合成意义的结构单元提供了一种实用的方法。值得注意的是,在整个反应序列中,在易感的α-手性中心均未发生外消旋作用。
更新日期:2016-12-27
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