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)CuII complexes. Different reaction pathways can be followed by different enol silyl ethers: with 2-(trimethylsilyloxy)furan, a MukaiyamaMichael adduct is obtained, whereas a hetero DielsAlder 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.
Enantioselective Addition of Cyclic Enol Silyl Ethers to 2-Alkenoyl-Pyridine-N-Oxides Catalysed by CuII-Bis(oxazoline) Complexes
LIVIERI, ALESSANDRO;BOIOCCHI, MASSIMO;DESIMONI, GIOVANNI;FAITA, GIUSEPPE
2012-01-01
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)CuII complexes. Different reaction pathways can be followed by different enol silyl ethers: with 2-(trimethylsilyloxy)furan, a MukaiyamaMichael adduct is obtained, whereas a hetero DielsAlder 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
