Tetrahedron letters

Zinc mediated addition of active halides to a glycine cation equivalent: synthesis of N-Boc-L-propargylglycine

NA Abood, R Nosal

Index: Abood, Norman A.; Nosal, Roger Tetrahedron Letters, 1994 , vol. 35, # 22 p. 3669 - 3672

Full Text: HTML

Citation Number: 19

Abstract

Abstract The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with α- chymotrypsin affords N-Boc-L-propargylglycine in 99% ee.

Related Articles:

Copper (I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles

[Witulski, Bernhard; Goessmann, Matthias Chemical Communications, 1999 , # 18 p. 1879 - 1880]

Synthesis of 1-alkyl-2-(trifluoromethyl) azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl) amines via intermediate azetidinium salts

[De Matteis, Valeria; Van Delft, Floris L.; Jakobi, Harald; Lindell, Stephen; Tiebes, Joerg; Rutjes, Floris P. J. T. Journal of Organic Chemistry, 2006 , vol. 71, # 20 p. 7527 - 7532]

Molecular modeling of γ-lactam analogues of β-lactam antibacterial agents: synthesis and biological evaluation of selected penem and carbapenem analoques

[Allen, Norris E.; Boyd, Donald B.; Campbell, Jack B.; Deeter, Jack B.; Elzey, Thomas K.; et al. Tetrahedron, 1989 , vol. 45, # 7 p. 1905 - 1928]

Asymmetric Synthesis of Monofluorinated 1-Amino-1, 2-dihydronaphthalene and 1, 3-Amino Alcohol Derivatives

[Luebke, Martin; Jung, Manfred; Haufe, Guenter Journal of Fluorine Chemistry, 2013 , vol. 152, p. 144 - 156]

Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

[Sakaitani, Masahiro; Ohfune, Yasufumi Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 870 - 876]

More Articles...