Chen Kang, Li Zhao-Wei, Shen Peng-Xiang, Zhao Hong-Wei, Shi Zhang-Jie
Beijing National Laboratory of Molecular Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of the Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing, 100871 (China).
Chemistry. 2015 May 11;21(20):7389-93. doi: 10.1002/chem.201406528. Epub 2015 Mar 24.
A novel bidentate α-amino oxazolinyl directing group has been developed. Different from previous directing groups, this newly designed directing group was easily prepared from amino acids and modified in structure. This auxiliary preferentially effects functionalization at secondary C(sp(3) )-H bonds, rather than at aryl C(sp(2) )-H bonds. The diastereoselectivity of direct arylation between geminal secondary C(sp(3) )-H bonds in linear molecules has also been realized for the first time with a chiral directing group by remote chirality relay. Two diastereoisomers are produced with the same chiral source by changing the substituents of substrates and aryl halides.
一种新型双齿α-氨基恶唑啉基导向基团已被开发出来。与先前的导向基团不同，这种新设计的导向基团很容易从氨基酸制备且结构可修饰。该助剂优先影响仲C(sp(3) )-H键的官能化，而非芳基C(sp(2) )-H键。通过远程手性传递，首次利用手性导向基团实现了线性分子中偕二仲C(sp(3) )-H键之间直接芳基化的非对映选择性。通过改变底物和芳基卤化物的取代基，由相同的手性源产生了两种非对映异构体。
