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Simple and Fast Synthesis of New Axially Chiral Bipyridine N,N′ ‐Dioxides for Highly Enantioselective Allylation of Aldehydes
Author(s) -
Kadlčíková Aneta,
Hrdina Radim,
Valterová Irena,
Kotora Martin
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900224
Subject(s) - enantioselective synthesis , chemistry , benzaldehyde , substrate (aquarium) , catalysis , bipyridine , combinatorial chemistry , tetrahydroisoquinoline , stereochemistry , organic chemistry , crystal structure , oceanography , geology
Unsymmetrically 3,3′‐substituted axially chiral bis(tetrahydroisoquinoline) N,N′‐ dioxides can be prepared in just three steps. They exhibit unique catalytic activity (turnover frequency, enantioselectivity, substrate scope) in the asymmetric allylation of aromatic aldehydes (up to 96% ee ). The product of the enantioselective allylation of benzaldehyde served as a building block for the preparation of an intermediate useful in the enantioselective synthesis of diospongines.