79516-58-8Relevant articles and documents
Enantioselective Construction of Modular and Asymmetric Baskets
Badji?, Jovica D.,Finnegan, Tyler J.,Gunther, Michael J.,Pavlovi?, Radoslav Z.,Wang, Xiuze
supporting information, p. 25075 - 25081 (2021/10/25)
The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive A-to-B and then AB-to-C Suzuki–Miyaura (SM) couplings were optimized to give enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so-called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo-responsive basket bearing one anthracene and two benzene arms.
The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand
Tanyeli, Cihangir,Oezcubukcu, Salih
, p. 1167 - 1170 (2007/10/03)
The asymmetric synthesis of trans-2,3-bis(aminomethyl)norbornane was performed starting with endo-2,3-norbornene dicarboxylate anhydride. Desymmetrization of meso-anhydride 1 and following selective epimerization gave the trans-monoester (+)-3 with a high enantiomeric excess (98% e.e.). LiAlH4 reduction of the trans-monoester to the 1,4-diol, which was then treated with phthalimide under Mitsunobu conditions and, following a Gabriel type amine synthesis with hydrazine hydrate, yielded a saturated and unsaturated diamine mixture. Hydrogenation of mixture finally afforded saturated diamine (+)-8 with a yield of 37%.
Stereoselectivity in the TiCl4-catalyzed [4 + 2] cycloaddition of cyclopentadiene to (2R)-bornane-10,2-sultam derivatives of fumaric acid monoesters
Achmatowicz, Michal,Chapuis, Christian,Rzepecki, Piotr,Jurczak, Janusz
, p. 182 - 190 (2007/10/03)
The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2- sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and π-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastere
