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Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes.

Chemistry (Weinheim an der Bergstrasse, Germany) (2012-08-01)
Alessandro Livieri, Massimo Boiocchi, Giovanni Desimoni, Giuseppe Faita
ABSTRACT

Asymmetric reactions involving (E)-3-aryl-1-(pyridin-2-yl-N-oxide)prop-2-en-1-ones and cyclic enol silyl ethers show good yields and excellent enantioselectivities (up to 99.9 % ee) when catalysed by bis(oxazoline)-Cu(II) complexes. Different reaction pathways can be followed by different enol silyl ethers: with 2-(trimethylsilyloxy)furan, a Mukaiyama-Michael adduct is obtained, whereas a hetero Diels-Alder cycloadduct was formed by using (1,2-dihydronaphthalen-4-yloxy)trimethylsilane. In the latter reaction, the absolute configuration of the product is consistent with a reagent approach to the less hindered Re face of the coordinated substrate in the reactive complex.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyridine N-oxide, 95%
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