d-Isomannide in synthesis: asymmetric Diels–Alder reactions with novel homochiral bis-imine Cu2+-catalysts

Pentafluorobenzaldehyde and its utilizing in organic synthesis

“…The PFBA reacts with aromatic amines in alcohol to afford high yields of Schiff bases (Scheme 43 [16,[482][483][484][485][486][487][488][489][490][491][492][493][494][495][496][497][498][499]). …”

Dianhydrohexitols: new tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes

“…[15][16][17][18] As a part of our ongoing program devoted to asymmetric catalysis, we were interested in the development of new chiral ligands derived from dianhydrohexitols (isomannide, isosorbide and isoidide). Ligands derived from dianhydroglycitols have already been used in organometallic catalysis to perform asymmetric Diels-Alder reactions, [19][20][21][22] nucleophilic addition to aldehyde, [23][24] hydrogen transfer reduction of prochiral ketones [25][26][27][28] and asymmetric hydrogenation of olefins. [29][30] However, to the best of our knowledge, none of them has been used in asymmetric organocatalysis.…”

Nitrogen-functionalized Isohexides in Asymmetric Induction

“…To date, the least accessible diamine 6 is synthesized in five steps from isomannide 2 in 43% yield via a diazide intermediate [25] which breaks the defined safety rules. [26] More recently, Beller reported a ruthenium-catalyzed amination of isosorbide through a borrowing hydrogen reaction leading to an inseparable diastereomeric mixture of diamines 4-6 in an excellent 96% yield.…”

“…Best enantioselectivity (ee 63%) was reached by complexation of copper (ii) triflate and bidentate ligands issued from coupling with 2,6-dichlorobenzaldehyde. [25] In contrast to the Diels-Alder reaction, asymmetric transfer hydrogenation in the presence of amino isohexides ligands, was investigated in more depth, mainly for the reduction of C=O bonds. The Rucatalyzed enantioselective reduction of acetophenone was reported with different sets of ligands and then followed by other aromatic ketones (Scheme 7).…”