The solid-state diastereoselective formation of oxazolidines

Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium‐Catalyzed Allylic Substitution

“…The diversity at the amino group wasa chieved by either direct methylation of 1-4 using formic acid and formaldehyde to afford 5-8 [12] (Scheme 1, step a) or by the formation of oxazolidine 9 [13] (Scheme 1, step b) from 1,f ollowed by ring-opening with the corresponding Grignardr eagents ( 10-11,step c). Amino alcohols 1-4 already incorporate the desired diversity in the substituents and in the configurations of the backbone.…”

Cymantrene-based iminodiamidophosphites: the first phosphite-type ligands with planar chirality

“…To a vigorously stirred solution of 1.14 g (0.003 mol) of (4S,5R)-3,4-dimethyl-5-phenyl-2-cymantrenyl-1,3-oxazolidine 28,29 in THF at À70°C was added 1.6 M solution of BuLi in hexane, 4 ml (0.0075 mol) for 10 min. The resulted mixture was stirred for another 1 h and solution of 1.64 g (0.0225 mol) of DMF in THF (100 ml) was added for 0.5 h. The resulted mixture was slowly heated to rt and 20% solution of H 3 PO 4 was added dropwise until pH = 7.…”

“…(2S,4S,5R)-3,4-dimethyl-5-phenyl-2-cymantrenyloxazolidine was prepared as published. 28,29 Phosphorylating reagents 2-chloro-1,3-diphenyl-1,3,2-diazaphospholidine and (2R,5S)-2-chloro-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octane were prepared according to previously described methods. 21,30 Rhodium complexes 6a and 6b, and 7a and 7b were synthesized for 31 P NMR and IR experiments in chloroform analogously to the known procedures.…”

Solid-state Suzuki reaction catalyzed by ferrocene palladacycles without solvent

“…Earlier we carried out the reaction of aryl bromides with phenylboric acid (3) in aqueous methanol in the pres ence of K 2 CO 3 and the catalyst. In this work, we per formed a series of experiments to reveal the possibility of interaction of acid 3 with aryl halides without any solvent in the presence of palladium complex 1 and K 2 CO 3 (Scheme 1, Table 1).…”