Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation
We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)oxy substituent. The transformations are best described mechanistically as intramolecular silatropic ene reactions based on stereoselectivity, kinetic and computed transition state data. The overall process constitutes a stereospecific (meth)allylation of α-hydroxyaldehydes, under neutral conditions, in which the hydroxyl protecting group is also the (meth)allylating agent.
Robertson, Jeremy,Hall, Michael J.,Green, Stuart P.
experimental part
p. 5541 - 5551
(2009/12/09)
Stereospecificity in the silicon tethered α-(methyl)allylation of aldehydes
Heating E- and Z-crotyl(diphenyl)silyloxy aldehydes, in the absence of an added catalyst, results in sterospecific intramolecular allyl transfer with moderate to high stereoselectivity. The successful preparation of suitable substrates was described to test the given proposal. This paper reports their behavior under both Lewis acidic and thermal conditions.
Robertson, Jeremy,Hall, Michael J.,Green, Stuart P.
p. 3635 - 3638
(2007/10/03)
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