4333-50-0Relevant articles and documents
Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates
Hu, Yue,Sun, Wei,Zhang, Tao,Xu, Nuo,Xu, Jianeng,Lan, Yu,Liu, Chao
supporting information, p. 15813 - 15818 (2019/10/28)
An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.
Synthesis and Reactions of Sulfenic Trifluoromethanesulfonic Anhydrides
Effenberger, Franz,Russ, Werner
, p. 3719 - 3736 (2007/10/02)
Sulfenyl halogenides 1 and 4 react with silver trifluoromethanesulfonate (2) to give aryl 3 and alkylsulfenic trifluoromethanesulfonic anhydrides 5, resp., in good yields; 3 and 5 could not be isolated because of their instability. 1H NMR spectroscopic data of 5a, b, each in dichloromethane and nitromethane, resp., are indicative of a dissoziation to adducts of alkylsulfenylium ions and the solvent.Whereas 3 do not react with aromatic compounds, addition products with diphenylacetylene, arylsulfenylvinyl trifluoromethanesulfonates 11, are formed smoothly, which under the reaction conditions immediately cyclize to give benzothiophenes 10 in excellent yields.