Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors

Science China Chemistry

Volumn 53, Issue 9, 2010, Pages 1921-1926

  Ayed, Charfedinne ^a   Picard, Julien ^a   Lubin Germain, Nadège ^a   Uziel, Jacques ^a   Auge, Jacques ^a  

^a Université Paris Seine   (France)

Author keywords

alkynyl iodides; alkynylation; amino acids; amino alcohols; C glycoside; indium; oxazolidines

Indexed keywords

ALKYNYLATIONS; ALKYNYLS; AMINO ALCOHOLS; C-GLYCOSIDE; OXAZOLIDINES;

ACETYLENE; ALCOHOLS; AMINES; BEARINGS (STRUCTURAL); CYCLOADDITION; INDIUM; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

AMINO ACIDS;

EID: 77957916800     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4072-2     Document Type: Conference Paper

References (17)

1. R. Duthaler 1994 Recent developments in the stereoselective synthesis of α-aminoacids Tetrahedron 50 1539 1650 1:CAS:528:DyaK2cXisVGksrw%3D 10.1016/S0040-4020(01)80840-1 (Pubitemid 24079001)
2. P. Garner J.M. Park 1987 The synthesis and configurational stability of differentially protected β-hydroxy-α-amino aldehydes J Org Chem 52 2361 2364 1:CAS:528:DyaL2sXktVOmt7Y%3D 10.1021/jo00388a004
3. P. Meffre S. Hermann P. Durand G. Reginato A. Riu 2002 Practical one-pot synthesis of ethynylglycine synthon from Garner's aldehyde Tetrahedron 58 5159 5162 1:CAS:528:DC%2BD38XksFKmtb0%3D 10.1016/S0040-4020(02)00438-6 (Pubitemid 34634207)
4. G. Reginato P. Meffre F. Gaggini 2005 Ethynylglycine synthon from Garner's aldehyde: A useful precursor for the synthesis of non-natural amino acids Amino Acids 29 81 87 1:CAS:528:DC%2BD2MXos1eltLw%3D 10.1007/s00726-005- 0184-y (Pubitemid 41191389)
5. S. Ohira 1989 Methanolysis of dimethyl(1-diazo-2-oxopropyl)phosphonate Generation of (diazomethyl) phosphonate ansd reaction with carbonyl compounds. Synth Commun 19 81 87
6. J. Augé N. Lubin-Germain L. Seghrouchni 2002 Indium-mediated carbonyl alkynylation Tetrahedron Lett 43 5255 5256 10.1016/S0040-4039(02)01052- 3 (Pubitemid 34717938)
7. J. Augé N. Lubin-Germain L. Seghrouchni 2003 Indium-mediated formation of propargyl ketones from aldehydes or acylchlorides Tetrahedron Lett 44 819 821 10.1016/S0040-4039(02)02635-7 (Pubitemid 36153255)
8. Picard J, Lubin-Germain N, Uziel J, Augé J. Indium mediated alkynylation in C-glycoside synthesis. Synthesis, 2006, 979-982
9. N. Lubin-Germain A. Hallonet F. Huguenot S. Palmier J. Uziel J. Augé 2007 Ferrier-type alkynylation reaction mediated by indium Org Lett 9 3679 3682 1:CAS:528:DC%2BD2sXosVWitLc%3D 10.1021/ol701480x
10. N. Lubin-Germain J.P. Baltaze A. Coste A. Hallonet H. Lauréano G. Legrave J. Uziel Augé 2008 Direct C-glycosylation by indium-mediated alkynylation on sugar anomeric position Org Lett 10 725 728 1:CAS:528: DC%2BD1cXhsVKlsLw%3D 10.1021/ol7029257
11. R. Aït Youcef M. Dos Santos S. Roussel J.P. Baltaze N. Lubin-Germain J. Uziel 2009 Huisgen cycloaddition reaction of C-alkynyl ribosides under micellar catalysis: Synthesis of ribavirin analogues J Org Chem 74 4318 4323 10.1021/jo900594x
12. A. Dondoni D. Perrone 2000 Synthesis of 1,1-dimethylethyl-(S)-4-formyl-2, 2-dimethyl-3-oxazolidine carboxylate by oxidation of the alcohol Org Synth 77 64 77 1:CAS:528:DC%2BD38XhsFCgsbY%3D
13. G.N. Wanyoike O. Onomura T. Maki Y. Matsumura 2002 Highly enhanced enantioselectivityin the memory of the chirality via acyliminium ions Org Lett 4 1875 1877 1:CAS:528:DC%2BD38XjtF2gsLw%3D 10.1021/ol025865r
14. A. Barco S. Benetti G. Spalluto A. Casolari G.P. Pollini V. Zanirato 1992 A new approach to kainoids through tándem Michael reaction methodology: Application to the enantioselective synthesis of (+)- and (-)-α-allokainic acid and to the formal synthesis of (-)-α-kainic acid J Org Chem 57 6279 6286 1:CAS:528:DyaK3sXit1Gmug%3D%3D 10.1021/jo00049a040 (Pubitemid 23003891)
15. Salvador BA, Solis FC. Derivatives of fusarochromanone as therapeutic agents. WO 2004/103985. 2004-2-12
16. Augé J, Lubin-Germain N, Uziel J. Recent advances in indium-promoted organic reactions. Synthesis, 2007, 1739-1764
17. Lasterra-Sanchez ME, Michelet V, Besnier I, Genêt JP. Convenient methods for the synthesis of β-C-glycosides. Synlett, 1994, 705-708