Table of Contents
Organic Chemistry International
Volume 2010, Article ID 452956, 3 pages
http://dx.doi.org/10.1155/2010/452956
Research Article

Directed Metalation of Heterocycles, 5-Methoxy-2-phenyloxazol-4-yllithium: An Approach to , -Dehydroamino Acids

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India

Received 1 July 2009; Accepted 16 September 2009

Academic Editor: Kirpal Bisht

Copyright © 2010 Sosale Chandrasekhar and Malempati Srimannarayana. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Snieckus, “Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics,” Chemical Reviews, vol. 90, no. 6, pp. 879–933, 1990. View at Google Scholar · View at Scopus
  2. R. Chinchilla, C. Nájera, and M. Yus, “Metalated heterocycles and their applications in synthetic organic chemistry,” Chemical Reviews, vol. 104, no. 5, pp. 2667–2722, 2004. View at Publisher · View at Google Scholar · View at Scopus
  3. G. L'abbé, A.-M. Ilisiu, W. Dehaen, and S. Toppet, “Synthesis and thermolysis of 5-azido-4-formyloxazoles,” Journal of the Chemical Society, Perkin Transactions 1, no. 19, pp. 2259–2261, 1993. View at Google Scholar · View at Scopus
  4. A. G. Griesbeck, S. Bondock, and J. Lex, “Synthesis of erythro-α-amino-β-hydroxy carboxylic acid esters by diastereoselective photocycloaddition of 5-methoxyoxazoles with aldehydes,” Journal of Organic Chemistry, vol. 68, no. 26, pp. 9899–9906, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Srimannarayana, Topics in synthetic methodology: from heterocycles to hydride transfers, Ph.D. thesis, Indian Institute of Science, Bangalore, India, 2009.
  6. K. Brocklehurst, R. P. Bywater, R. A. Palmer, and R. Patrick, “The crystal structure of the stable isomer of α-benzamidocinnamic acid: the influence of cis-trans-isomerism on the kinetics of the hydrolysis of the products of interaction of α-chymotrypsin with the isomeric 4-benzylidene-2-phenyl-Δ2-oxazolin-5-ones,” Journal of the Chemical Society D, no. 12, pp. 632–633, 1971. View at Publisher · View at Google Scholar · View at Scopus
  7. V. Busetti, D. Ajò, and A. Vittadini, “Structure of (Z)-N-benzoyl-α,β-dehydroleucine,” Acta Crystallographica Section C, vol. 42, no. 9, pp. 1178–1181, 1986. View at Google Scholar
  8. H. Takagaki, S. Tanabe, M. Asaoka, and H. Takei, “Reaction of 2-phenyl-5-trimethylsiloxyoxazole with carbonyl compounds or acetals: synthesis of α,β-dehydro-α-amino acid derivatives,” Chemistry Letters, vol. 8, no. 4, pp. 347–350, 1979. View at Google Scholar
  9. K. F. W. Hekking, D. C. J. Waalboer, M. A. H. Moelands, F. L. van Delft, and F. P. J. T. Rutjes, “A ring-closing metathesis approach to cyclic α,β-dehydroamino acids,” Advanced Synthesis & Catalysis, vol. 350, no. 1, pp. 95–106, 2008. View at Publisher · View at Google Scholar · View at Scopus
  10. F. Giacomina, A. Meetsma, L. Panella, L. Lefort, A. H. M. de Vries, and J. G. de Vries, “High enantioselectivity is induced by a single monodentate phosphoramidite ligand in iridium-catalyzed asymmetric hydrogenation,” Angewandte Chemie International Edition, vol. 46, no. 9, pp. 1497–1500, 2007. View at Publisher · View at Google Scholar · View at Scopus