An efficient asymmetric synthesis of Fmoc-L-cyclopentylglycine via diastereoselective alkylation of glycine enolate equivalent

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2683-2685

  Singh, Satendra ^a   Pennington, Michael W ^a  

^a Bachem Holding AG   (Switzerland)

Author keywords

Cyclopentylglycine; Fmoc L cyclopentylglycine; Glycine enolate equivalent

Indexed keywords

ALPHA AMINO ACID; BENZYL 6 OXO 2,3 DIPHENYL 4 MORPHOLINECARBOXYLATE; BENZYL 6 OXO 2,3 DIPHENYL 5 CYCLOPENTYL 4 MORPHOLINECARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTYLGLYCINE; CYCLOPENTYLIODIDE; GLYCINE DERIVATIVE; GLYCINE ENOLATE; IODIDE; LEAD CHLORIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037463744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00370-8     Document Type: Article

References (15)

1. Atkins J.F., Gesteland R. Science. 296:2002;1409-1410.
2. O'Donnell, M. J. (Ed.). α-Amino Acid Synthesis (Tetrahedron Symposium-in-Print). Tetrahedron 1988, 44, 5253-5614.
3. Williams R.M. The Synthesis of Optically Active α-Amino Acids. 7:1989;Pergamon Press, Oxford.
4. Duthaler R.O. Tetrahedron. 50:1994;1539-1650.
5. Seebach D., Sting A.R., Hoffmann M. Angew. Chem., Int. Ed. Engl. 35:1996;2708.
6. Schoellkopf U. Tetrahedron. 39:1983;2085-2091.
7. Seebach D., Juaristi E., Miller D.D., Schickli C., Weber T. Helv. Chim. Acta. 70:1987;237-261.
8. Williams R.M., Im M.-N. J. Am. Chem. Soc. 113:1991;9267-9286.
9. Oppolzer W., Moretti R., Zhou C. Helv. Chim. Acta. 77:1994;2363-2380.
10. Meyers A.G., Schnider P., Kwon S., Kung D.W. J. Org. Chem. 64:1999;3322-3327.
11. Harding W.M., Shire W.J. J. Biol. Chem. 206:1954;401-410.
12. Nyeki O., Szalay K.S., Kisfaludy L., Karpati E., Szporny L., Makara G.B., Varga B. J. Med. Chem. 30:1987;1719-1724.
13. Williams R.M., Sinclair P.J., Zhai D., Chen D. J. Am. Chem. Soc. 110:1988;1547-1557.
14. Dennis R.L., Plant W.J., Skinner C.G., Southerland G.L., Shive W. J. Am. Chem. Soc. 77:1955;2362-2364.
15. Dialer H., Steglich W., Beck W. Tetrahedron. 57:2001;4855-4861.