198402-59-4Relevant articles and documents
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 (2013/11/06)
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.
One-pot synthesis of aryl sulfones from alcohols
Murakami, Teiichi,Furusawa, Kiyotaka
, p. 479 - 482 (2007/10/03)
A one-pot synthesis of aryl sulfones from primary alcohols is described. Alcohols were treated with N-bromosuccinimide and triphenylphosphine, followed by addition of sodium arenesulfinate with a catalytic amount of tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.
1,2-Asymmetric Induction in the Zwitterionic Claisen Rearrangement of Allylamines
Nubbemeyer, Udo
, p. 3773 - 3780 (2007/10/02)
A zwitterionic Claisen rearrangement has been developed for optically active N-allylpyrrolidines using a two-phase system.The inherent-1,2 asymmetric induction was investigated for the generation of a new C-C bond adjacent to a chiral C-O function.The reaction with acetyl chloride led to a small diastereomeric excess, whereas the rearrangement with propionyl chloride proceeded with a high simple and a high induced diastereoselection.The resulting γ,δ-unsaturated amides were cyclized to the corresponding optically active γ-butyrolactones, which are useful intermediates in natural product synthesis.
