172223-20-0Relevant academic research and scientific papers
Reaction of methyl 4,5-epoxy-(2E)-pentenoate with arylcopper reagents
Nagumo,Irie,Akita
, p. 675 - 680 (2007/10/03)
The reaction of methyl 4,5-epoxy-(2E)-pentenoate (1) with various arylcopper reagents was studied. Basically, all arylcopper reagents react with 1 in SN2 fashion. However, addition of BF3 causes reversal of the regioselectivity, which can be ra
Synthesis of six-membered compounds by environmentally friendly cyclization using indirect electrolysis
Ihara, Masataka,Katsumata, Akira,Setsu, Fumihito,Tokunaga, Yuji,Fukumoto, Keiichiro
, p. 677 - 684 (2007/10/03)
[Ni(cyclam)](ClO4)2-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.
The Reaction of Methyl (E)-4,5-Epoxypent-2-enoate with Acylcopper: the Unique Role of Boron Trifluoride in determining Regioselectivity
Nagumo, Shinji,Irie, Shigeyuki,Akita, Hiroyuki
, p. 2001 - 2002 (2007/10/02)
Excess BF3 causes regioselectivity reversion in the reaction of methyl 4,5-epoxypent-2-enoate 1 with Ph2CuLi; this is rationalised by a two step conversion via methyl 4-bromo-5-hydroxypent-2-enoate 5.
