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Title: 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
Author: Teloxa, Saul F.
Mellado Hidalgo, Miguel
Kennington, Stuart C. D.
Romea, Pedro
Urpí Tubella, Fèlix
Aullón López, Gabriel
Font Bardia, Ma. Mercedes
Keywords: Síntesi asimètrica
Reacció aldòlica
Asymmetric synthesis
Aldol reaction
Issue Date: 1-Dec-2022
Publisher: Wiley-VCH
Abstract: 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.
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It is part of: Chemistry-A European Journal, 2022, vol. 28, num. 38, p. 1-10
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ISSN: 0947-6539
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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