Liebigs Annalen

On the preparation of β??amino acids from α??amino acids using the Arndt??Eistert reaction: Scope, limitations and stereoselectivity. Application to carbohydrate …

J Podlech, D Seebach

Index: Podlech, Joachim; Seebach, Dieter Liebigs Annalen, 1995 , # 7 p. 1217 - 1228

Full Text: HTML

Citation Number: 84

Abstract

Abstract The Arndt-Eistert homologation of α-amino acids was studied to determine the stereoselectivity in this reaction by chromatographic up-to-date analytical methods. While carba-mate-protected phenylglycine was transformed to the corresponding β-amino acid methyl ester with a stereoselectivity of only 9: 1, all other tested amino acid derivatives (Ala, Phe, Ser, Orn, tert-Leu and perhydro-azepine-2-carboxylic acid, suitably protected) were ...

Related Articles:

Synthesis of N-Methyl L-Phenylalanine for Total Synthesis of Pepticinnamin E

[Sun, Dequn; Zhang, Lingzi; Wang, Jin Asian Journal of Chemistry, 2012 , vol. 24, # 1 p. 319 - 322]

Synthesis of carbamates using yttria-zirconia based Lewis acid catalyst

[Pandey, Rajesh K.; Dagade, Sharda P.; Dongare, Mohan K.; Kumar, Pradeep Synthetic Communications, 2003 , vol. 33, # 23 p. 4019 - 4027]

Pd/C (en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations

[Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2000 , vol. 56, # 43 p. 8433 - 8441]

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]

Palladium catalyzed reductive deprotection of Alloc: Transprotection and peptide bond formation

[Beugelmans, Rene; Neuville, Luc; Bois-Choussy, Michele; Chastanet, Jacqueline; Zhu, Jieping Tetrahedron Letters, 1995 , vol. 36, # 18 p. 3129 - 3132]

More Articles...