Solid-phase synthetic method for (±)-α-amino acids via phase-transfer catalytic alkylation

Tetrahedron Letters

Volumn 46, Issue 1, 2005, Pages 93-95

  Park, Hyeung Geun ^a   Kim, Mi Jeong ^a   Park, Mi Kyung ^a   Jung, Hyun Ju ^a   Lee, Jihye ^a   Lee, Yeon Ju ^a   Jeong, Byeong Seon ^a   Lee, Jeong Hee ^a   Yoo, Mi Sook ^a   Ku, Jin Mo ^a   Jew, Sang Sup ^a  

^a Seoul National University   (South Korea)

Author keywords

Amino acid; Phase transfer catalytic alkylation; Solid phase synthesis

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; PHASE TRANSITION; SOLID; SYNTHESIS;

EID: 10044225569     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.020     Document Type: Article

References (25)

1. For lead references, see: Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium-in-Print, Hruby, V. J.; Soloshonok, V. A., Eds. Tetrahedron 2001, 57, 6329-6650
2. R.B. Merrifield J. Am. Chem. Soc. 85 1963 2419
3. R.B. Merrifield Science 232 1986 341
4. N.K. Terrett Combinatorial Chemistry 1998 Oxford University Press Oxford
5. F.Z. Dörwald Organic Synthesis on Solid Phase 2000 Wiley-VCH Verlag GmbH (Germany)
6. W. Bannwarth, and E. Felder Combinatorial Chemistry 2000 Wiley-VCH Verlag GmbH (Germany)
7. P. Seneci Solid-Phase Synthesis and Combinatorial Technologies 2000 John Wiley and Sons New York
8. M.J. O'Donnell, C. Zhou, and W.L. Scott J. Am. Chem. Soc. 118 1996 6070
9. W.L. Scott, C. Zhou, Z. Fang, and M.J. O'Donnell Tetrahedron Lett. 38 1997 3695
10. M.J. O'Donnell, C.W. Lugar, R.S. Pottorf, and C. Zhou Tetrahedron Lett. 38 1997 7163
11. D.L. Griffith, M.J. O'Donnell, R.S. Pottorf, W.L. Scott, and J.A. Porco Jr. Tetrahedron Lett. 38 1997 8821
12. E. Dorminguez, M.J. O'Donnell, and W.L. Scott Tetrahedron Lett. 39 1998 2167
13. M.J. O'Donnell, J.M. Boniece, and S.E. Earp Tetrahedron Lett. 19 1978 2641
14. M.J. O'Donnell, and T.M. Eckrich Tetrahedron Lett. 19 1978 4625
15. M.J. O'Donnell, and R.L. Polt J. Org. Chem. 47 1982 2663
16. M.J. O'Donnell Aldrichim. Acta 34 2001 3
17. -1
18. J.M. Frechet, and C. Schuerch J. Am. Chem. Soc. 93 1971 492
19. 4 and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, hexane-EtOAc = 10:1) to afford the desired product 10d as white solid
20. M.J. O'Donnell, and S. Wu Tetrahedron: Asymmetry 3 1992 591
21. B. Lygo, J. Crosby, and J.A. Perterson Tetrahedron Lett. 40 1999 8671
22. T. Ooi, M. Takeuchi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 122 2000 5228
23. S.-s. Jew, B.-S. Jeong, J.-H. Lee, M.-S. Yoo, Y.-J. Lee, B.-s. Park, and H.-g. Park J. Org. Chem. 68 2003 4514
24. +
25. The recovered resin 6A was confirmed by IR spectral data and successfully applied for the synthesis of α-amino acids