54008-70-7Relevant academic research and scientific papers
Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation
Robertson, Jeremy,Hall, Michael J.,Green, Stuart P.
experimental part, p. 5541 - 5551 (2009/12/09)
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.
Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines
Robertson, Jeremy,Stafford, Petra M.,Bell, Stephen J.
, p. 7133 - 7148 (2007/10/03)
We describe two applications of silicon-tethered thermal allyl transfer reactions of α-silyloxyaldehydes; formally, these processes can be regarded as silatropic carbonyl ene reactions in which the silicon tether is transferred to the aldehyde oxygen conc
Stereospecificity in the silicon tethered α-(methyl)allylation of aldehydes
Robertson, Jeremy,Hall, Michael J.,Green, Stuart P.
, p. 3635 - 3638 (2007/10/03)
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.
