1082605-50-2Relevant academic research and scientific papers
Reversal of facial selectivity in a thia-Claisen rearrangement by incorporation of a vinylic bromine substituent
Ellwood, Adam R.,Mortimer, Anne J. Price,Goodman, Jonathan M.,Porter, Michael J.
, p. 7530 - 7539 (2013)
Thia-Claisen rearrangements have been carried out using N-benzylpyrrolidine-2-thione and chiral allylic bromides derived from d-mannitol. Introduction of a bromine atom onto the double bond of the allylic bromide reverses the sense of diastereoselectivity in the [3,3]-sigmatropic rearrangement. Density functional theory calculations lead us to rationalise the observed selectivity in terms of a Cieplak effect.
Diastereoselective Thia-Claisen rearrangement of pyrrolidinone-derived ketene N,S-acetals
Ellwood, Adam R.,Price Mortimer, Anne J.,Tocher, Derek A.,Porter, Michael J.
scheme or table, p. 2199 - 2203 (2009/04/10)
Thia-Claisen rearrangements of S-allylic ketene N,S-acetals were carried out using substrates with an external allylic stereogenic centre. High levels of diastereoselectivity were observed only when a bromine substituent was introduced onto the double bon
