An asymmetric synthesis of anti-2,3-diamino acids is reported. The enolates of N,N-dibenzylated b3-amino esters were treated with di-tert-butyl azodicarboxylate (DBAD) to afford their N0,N00-di-Boc-2-hydrazino derivatives with excellent anti diastereoisomeric ratio. Final Boc removal and reductive cleavage of the hydrazino bond led to the expected 2,3-diamino esters having only one free amino group. In comparison with other asymmetric C-2 amination procedures, this method does not need the use of expensive chiral reagents and/or chiral auxiliaries, while leads to products which can be orthogonally protected.
Efficient Synthesis of ortogonally protected anti-2,3-diamino acids / Capone, Stefania; Guaragna, Annalisa; Palumbo, Giovanni; Pedatella, Silvana. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 63:49(2005), pp. 12202-12206. [10.1016/j.tet.2005.04.046]
Efficient Synthesis of ortogonally protected anti-2,3-diamino acids
CAPONE, STEFANIA;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI;PEDATELLA, SILVANA
2005
Abstract
An asymmetric synthesis of anti-2,3-diamino acids is reported. The enolates of N,N-dibenzylated b3-amino esters were treated with di-tert-butyl azodicarboxylate (DBAD) to afford their N0,N00-di-Boc-2-hydrazino derivatives with excellent anti diastereoisomeric ratio. Final Boc removal and reductive cleavage of the hydrazino bond led to the expected 2,3-diamino esters having only one free amino group. In comparison with other asymmetric C-2 amination procedures, this method does not need the use of expensive chiral reagents and/or chiral auxiliaries, while leads to products which can be orthogonally protected.File | Dimensione | Formato | |
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