91153-91-2Relevant academic research and scientific papers
A NEW SYNTHESIS OF trans-2-SUBSTITUTED-2-BUTENE-1,4-DIOLS FROM 2-BUTYNE-1,4-DIOL VIA NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS
Ishino, Yoshio,Wakamoto, Kohji,Hirashima, Tsuneaki
, p. 765 - 768 (1984)
trans-2-Substituted-2-butene-1,4-diols were readily obtained by reactions of 2-butyne-1,4-diol with Grignard reagents in good yields.
C-quaternary vinylglycinols by metal-catalyzed cyclization of allylic bistrichloroacetimidates
Klimovica, Kristine,Grigorjeva, Liene,Maleckis, Ansis,Popelis, Juris,Jirgensons, Aigars
supporting information; experimental part, p. 2849 - 2851 (2012/02/05)
Bistrichloroacetimidates derived from 2-substituted but-2-ene-1,4-diols are transformed into 4-substituted 4-vinyloxazolines in high yields and excellent regioselectivities when Lewis acids AlCl3, FeCl3, TMSOTf, BF3OEt2, and AgBF4 are used as catalysts as well as with the Pd(PPh3)2Cl2/AgBF4 catalytic system. Lower regioselectivity is achieved with a neutral PdCl 2(MeCN)2 catalyst and this could be a consequence of a switch to a competitive but less selective reaction mechanism. It is demonstrated that 4-substituted 4-vinyloxazolines can be efficiently transformed to N-Boc-protected C-quaternary vinylglycinols in a one-pot procedure. Georg Thieme Verlag Stuttgart · New York.
