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Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation of o ‐Alkynylacetophenones
Author(s) -
Saito Kodai,
Kajiwara Yuki,
Akiyama Takahiko
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308303
Subject(s) - enantioselective synthesis , intramolecular force , catalysis , copper , transfer hydrogenation , chemistry , phosphate , ylide , combinatorial chemistry , computer science , organic chemistry , ruthenium
A good mix : The title reaction of o ‐alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.