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Simple and Fast Synthesis of New Axially Chiral Bipyridine N,N′-Dioxides for Highly Enantioselective Allylation of Aldehydes

✍ Scribed by Aneta Kadlčíková; Radim Hrdina; Irena Valterová; Martin Kotora

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
185 KB
Volume
351
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

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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.

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