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Palladium‐Catalyzed Asymmetric Aminohydroxylation of 1,3‐Dienes
Author(s) -
Shen HongCheng,
Wu YuFeng,
Zhang Ying,
Fan LianFeng,
Han ZhiYong,
Gong LiuZhu
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712350
Subject(s) - regioselectivity , chemistry , tosyl , palladium , catalysis , oxazoline , yield (engineering) , ligand (biochemistry) , reagent , combinatorial chemistry , enantioselective synthesis , organic chemistry , materials science , biochemistry , receptor , metallurgy
A Pd II ‐catalyzed asymmetric aminohydroxylation of 1,3‐dienes with N‐tosyl‐2‐aminophenols was developed by making use of a chiral pyridinebis(oxazoline) ligand. The highly regioselective reaction provides direct and efficient access to chiral 3,4‐dihydro‐2 H ‐1,4‐benzoxazines in high yield and enantioselectivity (up to 96:4 e.r.). The reaction employs readily available N‐tosyl‐2‐aminophenols as a unique aminohydroxylation reagent and is complementary to known asymmetric aminohydroxylation methods.