921-48-2Relevant articles and documents
Forming Stereogenic Centers in Acyclic Systems from Alkynes
Vabre, Roxane,Island, Biana,Diehl, Claudia J.,Schreiner, Peter R.,Marek, Ilan
supporting information, p. 9996 - 9999 (2015/08/19)
The combined carbometalation/zinc homologation followed by reactions with α-heterosubstituted aldehydes and imines proceed through a chair-like transition structure with the substituent of the incoming aldehyde residue preferentially occupying a pseudo-axial position to avoid the two gauche interactions. The heteroatom in the axial position produces a chelated intermediate (and not a Cornforth-Evans transition structure for α-chloro aldehydes and imines) leading to a face differentiation in the allylation reaction. This method provides access to functionalized products in which three new carbon-carbon bonds and two to three stereogenic centers, including a quaternary one, were created in acyclic systems in a single-pot operation from simple alkynes. All-carbon quaternary stereocenter: The combined carbometalation/zinc homologation of alkynes followed by reactions with α-heterosubstituted aldehydes and imines provides access to functionalized acyclic adducts. These adducts obtained in a single-pot reaction have three new carbon-carbon bonds and two to three stereogenic centers, including a quaternary carbon stereocenter.
Stereoselective synthesis of chiral 4-(1-Chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines
Dekeukeleire, Stijn,Dhooghe, Matthias,Toernroos, Karl W.,De Kimpe, Norbert
experimental part, p. 5934 - 5940 (2010/11/05)
Chiral short-chain α-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic α-chlorination procedures. The latter aldehydes proved
Design of siloxane liquid crystals forming a de vries SmA* phase
Galli,Reihmann,Crudeli,Chiellini,Panarin, Yu,Vij,Blanc,Lorman,Olsson
, p. 245/2111-257/2123/ (2007/10/03)
We designed and synthesized new SmA* liquid crystals with different molecular architectures based on the chiral mesogen MR11, which was unsubstituted, or attached at one end and at both ends of a trisiloxane segment in the monosubstituted MSi3-MR11 and disubstituted DSi3-MR11 siloxanes, respectively. We studied the critical divergence of the magnetic susceptibility by measurements of the induced tilt angle θind at the SmA*-SmC* transition. While all three SmA* liquid crystals presented a de Vries character, this was quite distinctive for DSi3-MR11 for which the critical exponent γ = 1.87 was maximal. X-ray diffraction experiments confirmed that the SmA*-SmC* transition occurred with essentially no layer shrinkage.