Premium
Efficient Catalytic Enantioselective Hydroxyamination of α‐Aryl‐α‐Cyanoacetates with 2‐Nitrosopyridines
Author(s) -
Zhang Jingchuan,
Fu Kai,
Lin Lili,
Lu Yan,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2018
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.201800592
Subject(s) - enantioselective synthesis , catalysis , aryl , chemistry , mathematics , organic chemistry , alkyl
The highly enantioselective totally N‐selective hydroxyamination reaction of α‐aryl‐α‐cyanoacetates with 2‐nitrosopyridines was realized by using a chiral N , N′ ‐dioxide/Mg(OTf) 2 complex as catalyst, which enriches the nitroso chemistry. A variety of 2‐cyano‐2‐[hydroxyl(pyrydin‐2‐yl)amino]acetates with quaternary stereocenters and potential antibacterial activities were obtained in excellent yields with good to excellent ee values under as low as 0.05 mol % catalyst loading. The products could be easily transformed to useful α‐amino amides and 1,2‐diamines. Besides, a possible transition state model was proposed to elucidate the origin of the chirality induction.