2026-04-13T01:22:33Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/1915862025-12-04T21:42:28Zcom_2072_1057col_2072_478917col_2072_478933

00925njm 22002777a 4500 dc Teloxa, Saul F. author Mellado Hidalgo, Miguel author Kennington, Stuart C. D. author Romea, Pedro author Urpí Tubella, Fèlix author Aullón López, Gabriel author Font Bardia, Ma. Mercedes author 2022-12-14T16:49:00Z 2022-12-14T16:49:00Z 2022-12-01 2022-12-14T16:49:01Z A direct and asymmetric triisopropylsilyltrifluoromethanesulfonate (TIPSOTf) mediated aldol reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with aromatic aldehydes catalyzed by a chiral nickel(II)-Tol-BINAP complex has been developed (BINAP=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl). The catalytic protocol gives the corresponding anti α-azido-β-silyloxy adducts with outstanding stereocontrol and in high yields. Theoretical calculations account for the stereochemical outcome of the reaction and lay the foundations for a mechanistic model. In turn, the easy removal of the thiazolidinethione yields a wide array of enantiomerically pure derivatives in a straightforward and efficient manner. Such a noteworthy character of the heterocyclic scaffold together with the appropriate manipulation of the azido group open a new route to the synthesis of di- and tripeptide blocks containing a β-aryl-β-hydroxy-α-amino acid. Síntesi asimètrica Níquel Reacció aldòlica Asymmetric synthesis Nickel Aldol reaction Direct and Asymmetric Aldol Reactions of N-Azidoacetyl-1,3-thiazolidine-2-thione Catalyzed by Chiral Nickel(II) Complexes. A New Approach to the Synthesis of -Hydroxy--Amino Acids