1617-32-9Relevant articles and documents
A Facile Method for the Sulfenyllactonization of Alkenoic Acids Using Dimethyl Sulfoxide Activated by Oxalyl Chloride
Zhang, Ting,Dai, Yifeng,Cheng, Siwei,Liu, Yongguo,Yang, Shaoxiang,Sun, Baoguo,Tian, Hongyu
, p. 1380 - 1386 (2017)
A simple approach has been developed for the sulfenyllactonization of alkenoic acids using dimethyl sulfoxide activated with oxalyl chloride, in which methanesulfenyl chloride is proposed as the intermediate.
THE BARRIER FOR 1,2 HYDROGEN SHIFT IN DIALKYL CARBENES
Stevens, Ian D. R.,Liu, Michael T. H.,Soundararajan, N.,Paike, N.
, p. 481 - 484 (1989)
The products from the thermolysis of 4-diazirinopentanoic acid (2) allow the estimate of an experimental value for the Ea = 1.1 +/- 1 kcal.mol-1 for the barrier height for 1,2 H shift in dialkyl carbenes.
Khasanov et al.
, (1979)
Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3
Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto
supporting information, p. 1961 - 1965 (2021/01/04)
Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.
Regioselective Isomerization of Terminal Alkenes Catalyzed by a PC(sp3)Pincer Complex with a Hemilabile Pendant Arm
De-Botton, Sophie,Filippov, D.Sc. Oleg A.,Shubina, Elena S.,Belkova, Natalia V.,Gelman, Dmitri
, p. 5959 - 5965 (2020/10/15)
We describe an efficient protocol for the regioselective isomerization of terminal alkenes employing a previously described bifunctional Ir-based PC(sp3)complex (4) possessing a hemilabile sidearm. The isomerization, catalyzed by 4, results in a one-step shift of the double bond in good to excellent selectivity, and good yield. Our mechanistic studies revealed that the reaction is driven by the stepwise migratory insertion of Ir?H species into the terminal double bond/β-H elimination events. However, the selectivity of the reaction is controlled by dissociation of the hemilabile sidearm, which acts as a selector, favoring less sterically hindered substrates such as terminal alkenes; importantly, it prevents recombination and further isomerization of the internal ones.
