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Development of Modifiable Bidentate Amino Oxazoline Directing Group for Pd‐Catalyzed Arylation of Secondary CH Bonds
Author(s) -
Chen Kang,
Li ZhaoWei,
Shen PengXiang,
Zhao HongWei,
Shi ZhangJie
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406528
Subject(s) - oxazoline , geminal , chemistry , diastereomer , aryl , denticity , chirality (physics) , catalysis , molecule , planar chirality , stereochemistry , axial chirality , group (periodic table) , halide , combinatorial chemistry , enantioselective synthesis , organic chemistry , alkyl , crystal structure , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
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.