Shenyang Pharmaceutical University , 103 Wenhua Lu, Shenyang 110016, China.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Org Lett. 2017 Jan 6;19(1):246-249. doi: 10.1021/acs.orglett.6b03548. Epub 2016 Dec 27.
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.
利用钯催化的导向 C-H 官能化反应，实现了（S）-N-Boc-2,6-二甲基酪氨酸的简短高效合成。这代表了酪氨酸衍生物邻位二甲化的首例通用方法，并为制备这一具有重要合成意义的砌块提供了实用方法。值得注意的是，在整个反应序列中，易位的 α-手性中心没有发生外消旋化。
