114467-53-7Relevant academic research and scientific papers
Regioselective SN2 opening of α,β-ethylenic epoxides by RLi-BF3 combination
Alexakis, Alexandre,Vrancken, Emmanuel,Mangeney, Pierre,Chemla, Fabrice
, p. 3352 - 3353 (2000)
Organolithium reagents effect a regioselective SN2 nucleophilic cleavage of α,β-ethylenic epoxides only when BF3·Et2O is added. The reaction works with a variety of RLi reagents and with cyclic as well as acyclic epoxides. The Royal Society of Chemistry 2000.
Installation of carbon chain onto 2-cyclohexene-1,4-diol monoacetate
Abbas, Ashraf A.,Kobayashi, Yuichi
, p. 119 - 122 (2003)
Alkylation of cyclohexenyl monoacetate 1 with R2Cu(CN)(MgCl)2 or RMgBr/CuCN (cat.) in Et2O produced trans 1,2-isomers 4, while arylation and alkenylation of 1 was accomplished with lithium borates 5 and a nickel cat. to af
Palladium pincer complex catalyzed cross-coupling of vinyl epoxides and aziridines with organoboronic acids
Kjellgren, Johan,Aydin, Juhanes,Wallner, Olov A.,Saltanova, Irina V.,Szabo, Kalman J.
, p. 5260 - 5268 (2007/10/03)
Palladium-catalyzed crosscoupling of vinyl epoxides and aziridines with organoboronic acids was performed by using 0.5-2.5 mol % pincer-complex catalyst. The reactions proceed under mild conditions affording allyl alcohols and amines with high regioselectivity and in good to excellent yields. Under the applied reaction conditions aromatic chloro-, bromoand iodo substituents are tolerated. Our results indicate that the mechanism of the pincer complex catalyzed and the corresponding palladium(O) catalyzed process is substantially different. It was concluded that the transformations proceed via transmetalation of the organoboronic acids to the pincercomplex catalyst followed by an S N2′type opening of the vinyl epoxide or aziridine substrate. In this process the palladium atom is kept in oxidation state +2 under the entire catalytic process, and therefore oxidative side reactions can be avoided.
PALLADIUM CATALYZED COUPLING OF ORGANOSTANNANES WITH VINYL EPOXIDES
Tueting, David R.,Echavarren, Antonio M.,Stille, J. K.
, p. 979 - 992 (2007/10/02)
The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product.Both aryl- and vinylstannanes undergo coupling in high yields, wh
