271600-36-3Relevant articles and documents
Ruthenium Metathesis: A Key Step to Access a New Cyclic Tetrasubstituted Olefin Platform
Heinrich, Clément F.,Durand, Didier,Starck, Jér?me,Michelet, Véronique
supporting information, p. 7064 - 7067 (2020/08/24)
An rapid and mild synthetic route for the preparation of cyclic tetrasubstituted platforms via ruthenium-catalyzed ring-closing metathesis (RCM) has been developed. This process tolerates a wide range of functionalities such as nitrogen, oxygen, sulfur, silicon, and carbon tethered groups, as well as very challenging fluorine and boron atoms (36 derivatives, up to 96%). This diversity-oriented method was further demonstrated by the postfunctionalization reactions, such as Pd-couplings, N-substitution, and reductive amination introducing a morpholine moiety.
Leaving group and regioselectivity switches in the aminoalkylation reaction of indoles and related heterocycles with α-amido sulfones
Blay, Gonzalo,Giron, Rosa M.,Montesinos-Magraner, Marc,Pedro, Jose R.
supporting information, p. 3885 - 3895 (2013/07/19)
The regioselective aminoalkylation of indoles and related heterocycles with α-amido sulfones under basic conditions has been studied. The reaction that employed the MeMgBr/MgBr2 system provided high yields of 3-(1-carbamoylalkyl)indoles. On the other hand, the reaction that used Cs 2CO3 afforded 1-(1-carbamoylalkyl)indoles exclusively in high yields. The first reaction constitutes a switch of the leaving group of the α-amido sulfone in comparison to previously reported reactions between indoles and α-amido sulfones, which provided 3-(1-arylsulfonylalkyl) indoles. The second reaction constitutes a switch in the regioselectivity. The extensions of these C- and N-aminoalkylations starting from pyrroles and 7-azaindole have also been studied. Structurally diverse aminoalkylated indoles, pyrroles, and 7-azaindoles were obtained with excellent yield in most of the cases. The regioselective aminoalkylation of indoles and heterocycles with α-amido sulfones under basic conditions is described. The reaction with MeMgBr/MgBr2 gives 3-(1-carbamoylalkyl)indoles, whereas employing Cs2CO3 yields 1-(1-carbamoylalkyl)indoles. The first case presents a switch of the leaving group of the α-amido sulfone, whereas the second demonstrates a switch in the regioselectivity. Copyright
Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines
Vyas, Devendra J.,Froehlich, Roland,Oestreich, Martin
supporting information; experimental part, p. 2094 - 2097 (2011/06/22)
Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.
