Helvetica Chimica Acta

Highly Enantioselective Synthesis of Orthogonally Protected (2S)??2, 3??Diaminopropanoates through Catalytic Phase??Transfer Aza??Henry Reaction

G Kumaraswamy, A Pitchaiah

Index: Kumaraswamy, Gullapalli; Pitchaiah, Arigala Helvetica Chimica Acta, 2011 , vol. 94, # 8 p. 1543 - 1550

Full Text: HTML

Citation Number: 16

Abstract

Abstract The syntheses of enantiomer-enriched orthogonally protected different (2S)-2, 3- diaminopropanoates and unnatural furyl-substituted (tert-butoxy) carbonyl (Boc) as well as (benzyloxy) carbonyl (Cbz) protected amino acid esters are accomplished by means of an enantioselective aza-Henry reaction. A key feature of this protocol is organocatalysis as a genesis of chirality to ensure high enantioselectivity.

1235352-41-6

Boc-β-nitro-Ala-OMe

~84%

~73%

Assessing the Rates of Ring-Opening of Aziridinium and Azeti...

[Couturier, Cedric; Blanchet, Jerome; Schlama, Thierry; Zhu, Jieping Organic Letters, 2006 , vol. 8, # 10 p. 2183 - 2186]

Iridium??Catalyzed Asymmetric Allylic Amination with Polar A...

[Tosatti, Paolo; Horn, Joachim; Campbell, Amanda J.; House, David; Nelson, Adam; Marsden, Stephen P. Advanced Synthesis and Catalysis, 2010 , vol. 352, # 18 p. 3153 - 3157]

Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives ...

[Lherbet, Christian; Morin, Mylene; Castonguay, Roselyne; Keillor, Jeffrey W. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 6 p. 997 - 1000]

A Selective Protection of 2, 3-Diaminopropionic Acid

[Synthetic Communications, , vol. 23, # 5 p. 703 - 709]

Synthesis and Biological Activity of (S)-2-Amino-3 (2, 5-dih...

[Chemical and Pharmaceutical Bulletin, , vol. 39, # 5 p. 1199 - 1212]