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Chiral Silver Phosphate Catalyzed Transformation of ortho ‐Alkynylaryl Ketones into 1 H ‐Isochromene Derivatives through an Intramolecular‐Cyclization/Enantioselective‐Reduction Sequence
Author(s) -
Terada Masahiro,
Li Feng,
Toda Yasunori
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307371
Subject(s) - enantioselective synthesis , chemistry , intramolecular force , yield (engineering) , catalysis , sequence (biology) , transformation (genetics) , stereochemistry , molecule , phosphate , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , biochemistry , metallurgy , gene
The transformation of ortho ‐alkynylaryl ketones through a cyclization/enantioselective‐reduction sequence in the presence of a chiral silver phosphate catalyst afforded 1 H ‐isochromene derivatives in high yield with fairly good to high enantioselectivity. An asymmetric synthesis of the 9‐oxabicyclo[3.3.1]nona‐2,6‐diene framework, which has been found in some biologically active molecules, is presented as a demonstration of the synthetic utility of this method.