Premium
Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers
Author(s) -
Tan Qiuyuan,
Wang Xinqiao,
Xiong Yang,
Zhao Zimeng,
Li Lu,
Tang Pei,
Zhang Min
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700581
Subject(s) - stereocenter , alcohol , chirality (physics) , reactivity (psychology) , chemistry , amino acid , quaternary carbon , carbon fibers , nitrogen , stereochemistry , catalysis , combinatorial chemistry , enantioselective synthesis , organic chemistry , materials science , biochemistry , medicine , chiral symmetry breaking , physics , alternative medicine , pathology , quantum mechanics , quark , composite number , nambu–jona lasinio model , composite material
We have developed a highly efficient asymmetric allylboration of ketimines with nonchiral γ,γ‐disubstituted allylboronic acids by using a chiral amino alcohol as the directing group, which is otherwise challenging. The amino alcohol not only serves as a cheap source of nitrogen and chirality, but also dramatically enhances the reactivity. The versatility of this method was demonstrated by its ability to access all four stereoisomers with adjacent quaternary carbon centers. A reaction model was proposed to explain the diastereoselectivity and the rate‐accelerating effect.