126274-79-1Relevant academic research and scientific papers
Single-electron/pericyclic cascade for the synthesis of dienes
Campbell, Natalie E.,Sammis, Glenn M.
supporting information, p. 6228 - 6231 (2014/06/23)
The highly efficient and diastereoselective synthesis of E dienes has been accomplished through radical cyclization of bromoallyl hydrazones. This methodology has been further extended to generate these products through a one-pot condensation/radical cyclization/cycloreversion cascade from simple aldehyde starting materials in high yields (>75 %) and high diastereoselectivities (>95:5). Mechanistic investigations suggest that the cascade reaction proceeds through a cyclic diazene intermediate prior to the cycloreversion.
Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: Total synthesis of psymberin
Byeon, Seong Rim,Park, Heekwang,Kim, Hyoungsu,Hong, Jiyong
supporting information; experimental part, p. 5816 - 5819 (2012/01/06)
The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of α,β-un
Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes
Ide, Mitsuaki,Nakata, Masaya
, p. 2491 - 2499 (2007/10/03)
2-Substituted 1,3-dithiane derivatives, (S)-1(t-butyldiphenylsiloxy)-2- (1,3-dithian-2-yl)propane (9), (S)-1-(t-butyldimethylsiloxy)-2-(1,3-dithian- 2-yl)propane, 1-(t-butyldiphenylsiloxy)-2-(1,3-dithian-2-yl)-2-methylpropane, and 1,2-bis-(t-butyldiphenylsiloxy)-3-(1,3-dithian-2-yl)propane, were subjected to lithiation in THF with n-BuLi at room temperature (r.t.); the resulting anions reacted with 2,3-disubstituted oxirane, trans-2-methyl-3- (triphenylmethoxymethyl)oxirane(22), at r.t., giving the coupling products in satisfactory yield. On the other hand, the lithium salt formed in ether from (S)2-(1,3-dithian-2-yl)-1-(4-methoxybenzyloxy)propane with n-BuLi at r.t. reacted with 22 at r.t. in the presence of hexamethylphosphoric triamide to afford the coupling product in moderate yield. In addition, a mixed organometallic reagent, n-BuLi/Bu2Mg, was found to be an effective metallation reagent for 9 and the resulting anion reacted with 22 to afford the coupling product in good yield.
Generation of 2-substituted-2-metallo-1,3-dithianes and their coupling with 1,2-disubstituted epoxides at room temperature
Ide, Mitsuaki,Yasuda, Minora,Nakata, Masaya
, p. 936 - 938 (2007/10/03)
2-Substituted-1,3-dithianes were subjected to lithiation by n-BuLi at room temperature and the resulting anions reacted with 1,2-disubstituted epoxides at room temperature, giving the coupling products in satisfactory yield. In addition, a mixed organomet
Insight into the Cyclization of 6-Octen-1-als with Rhodium(I) Complex
Funakoshi, Kazuhisa,Togo, Nagako,Koga, Ichiro,Sakai, Kiyoshi
, p. 1990 - 1994 (2007/10/02)
Cyclization of 6-octen-1-als with Rh(I) (Wilkinson) complex was examined.In all cases with methyl substituents at the C2- or C3-position, a mixture of cis- and trans-cyclohexanol derivatives was obtained, but 7-methyl-6-octen-1-al without any substituents instead underwent a decarbonylation reaction. 4-Oxa-analogues also afforded a similar result.In Rh(I)-catalyzed cyclization, the formation of cis-cyclohexanols is in remarkable contrast to Lewis acid-catalyzed cyclization to afford the trans products.
