Phosphorus-Containing Chiral Macrocycles

Enantioselective recognition of an inherently chiral calix[4]arene crown-6 carboxylic acid cone conformer towards chiral aminoalcohols

“…The concept of "inherent chirality" was rst introduced by Böhmer in 1994 to describe calix [4]arene-based species which exhibit holistic chirality due to the absence of a plane of symmetry or an inversion center rather than to a local stereogenic center. 1 Since then, much effort has been devoted to the synthesis and application of enantiopure inherently chiral calixarenes, and related species such as resorcinarenes, and cyclotriveratrylenes.…”

Pd(0)-Сatalyzed Amination in the Synthesis of Planar-Chiral Macrobicyclic Compounds Comprising 1,5-Disubstituted Anthraquinone Moiety

“…It is noteworthy that the application of another chiral ligand with more electron-rich substituents at the phosphorus atom, namely Josiphos SL-J009-2, provided both poorer chemical and optical yields of the macrocycle (entry 5). Note that the macrocyclization with trioxadiamine 2c in the presence of Pd(dba) 2 /Josiphos SL-J002-2 (8/9 mol%) gave smaller yield of the product (18 %) but provided higher enantioselectivity (66 %) compared to the result with 16/18 mol% of the same catalytic system (entries 8,9). The reaction with the longest tetraoxadiamine 2d was quite successful with rac-BINAP as a ligand (entry 10) and not only the target macrocycle 3d-r but also linear oligomers 4d and 5d were isolated, but the result with chiral ligand was more modest and enantioselectivity reached only 34 % (entry 11).…”

“…They include the compounds which are based on chiral diamines and Schiff bases, [3][4][5] contain amino acid fragments, [6] in other molecules macrocycles are cyclocondensed with chiral skeletons, [7] usually such molecules comprise oxygen and nitrogen donor atoms, and also phosphorus-containing chiral macrocycles have been described. [8][9][10] Planar-chiral macrocycles are still quite rare. [11][12][13] Until last time macrocycles with BINOL C2-chiral moiety have been of constant interest.…”

A convenient synthesis of 2,7-dioxa-5,10-diaza-3λ5,8λ5-diphospha-1,6(1,4)-dibenzenacyclodecaphanes

“…Therefore, much attention is given to the development of methods of synthesis of such compounds [1][2][3][4][5][6][7].…”

“…Therefore, much attention is given to the development of methods of synthesis of such compounds [1][2][3][4][5][6][7].We previously showed for the first time [8] that p-(benzylideneamino)phenol in the absence of other bases reacts with dialkyl phosphorochloridites in chloroform to give phosphorus-containing [4.4]paracyclophane analogs. The present communication reports on the results of analogous reactions with substituted iminophenols both in the absence (Scheme 1) and in the presence of other base (Scheme 2).…”