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Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes
Author(s) -
Ma Chun,
Zhou JiaYu,
Zhang YiZhu,
Mei GuangJian,
Shi Feng
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801349
Subject(s) - enantioselective synthesis , isatin , catalysis , chemistry , yield (engineering) , combinatorial chemistry , organic chemistry , materials science , metallurgy
The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee ). The developed reaction has not only established a catalytic enantioselective [2+3] cyclization using azlactones as two‐carbon building blocks, but also enriches the chemistry of catalytic asymmetric cyclizations of azonaphthalenes. In addition, this protocol will provide a useful method for constructing enantioenriched 3,3′‐disubstituted isatin‐type frameworks.