Tetrahedron Letters

Synthesis of N-protected α-amino aldehydes from their morpholine amide derivatives

C Douat, A Heitz, J Martinez, JA Fehrentz

Index: Douat, Celine; Heitz, Annie; Martinez, Jean; Fehrentz, Jean-Alain Tetrahedron Letters, 2000 , vol. 41, # 1 p. 37 - 40

Full Text: HTML

Citation Number: 50

Abstract

A new method for the synthesis of N-protected α-amino aldehydes was developed. N- Protected α-amino amides of morpholine were easily prepared and then reduced with LiAlH4 to produce clean N-protected α-amino aldehydes. This new scheme of synthesis can be used with Boc, Z and Fmoc amino-protecting groups.

Related Articles:

Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A

[Conroy, Trent; Guo, Jin T.; Linington, Roger G.; Hunt, Nicholas H.; Payne, Richard J. Chemistry - A European Journal, 2011 , vol. 17, # 48 p. 13544 - 13552]

Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs)

[Fehrentz, Jean-Alain; Pothion, Catherine; Califano, Jean-Christophe; Loffet, Albert; Martinez, Jean Tetrahedron Letters, 1994 , vol. 35, # 48 p. 9031 - 9034]

Preparation of N 2-protected amino acid aldehydes via reduction of corresponding acid halides with lithium tris-(tert. butoxy)-aluminium hydride

[Zlatoidsky, Pavol Tetrahedron Letters, 1995 , vol. 36, # 40 p. 7281 - 7284]

Chiral aminal termplates 6 1. Diastereoselectivity of hydrazone alkylation. Asymmetric synthesis of α-aminoaldehydes

[Alexakis, Alexandre; Lensen, Nathalie; Mangeney, Pierre Tetrahedron Letters, 1991 , vol. 32, # 9 p. 1171 - 1174]

Synthesis of conjugated allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and aryl-or alkenylboronates

[Organic Letters, , vol. 14, # 3 p. 816 - 819]

More Articles...