3-tert-Butyldimethylsilyloxymethyl-2-lithio-2-phenylsulfonyloxirane as a glycidyl anion equivalent; preparation of terminal epoxy ketones

Synthesis and crystal structures of 2-substituted-2-phenylsulfonyloxiranes: evidence for a generalised anomeric effect in 2-phenylsulfonyloxiranesElectronic supplementary information (ESI) available: PDB files of the crystal structures of compounds 5, 6b and 7. See http://www.rsc.org/suppdata/ob/b3/b301409f/

“…General experimental procedures have been previously described. 11 All NMR spectra were recorded in CDCl 3 as solvent. J values are given in Hz.…”

Development of New Synthetic Methods Using Oxiranyl Anions and Application in the Syntheses of Polycyclic Ether Marine Natural Products

“…Initial studies on α-lithiated epoxy sulfones were performed by Jackson's group between the late 1980 s and early 1990 s. [24][25][26][27][28] We reinvestigated the reaction of the oxiranyl anion of epoxy sulfones because the strong electron-withdrawing nature of the sulfonyl group predicts that it may be a good anion-stabilizing group as well as a good leaving group after reaction with electrophiles, where the sulfonyl group needs to be removed for further elaboration into target molecules.…”

Recent Developments in the Chemistry of Lithiated Epoxides

“…62 This chemistry allowed the convergent synthesis of a range of 2-cyano-1,3-dienes 112 (Scheme 40). Following on from the extensive studies of phenylsulfonyl-stabilised lithiated epoxides by Jackson et al, [63][64][65][66][67][68][69] Mori has reported the ability of these stabilised anions to be trapped with substituted alkyl iodides and triflates, as well as epoxides (Scheme 41). 70,71 As previously reported, these stabilised anions are configurationally stable.…”