Erythrulose derivatives as functionalized chiral d3 and d4 synthons

Author:

Murga Juan,Falomir Eva,Carda Miguel,Marco J.Alberto

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference29 articles.

1. Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters

2. Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron: Asymmetry 2000, 11, 3211–3220. For a chiral d1 synthon type in a ketone related to erythrulose, see: Carda, M.; González, F.; Sánchez, R.; Marco, J. A. Tetrahedron: Asymmetry 2002, 13, 1005–1010.

3. For representative examples of d2 chiral synthons, see: (a) Takai, K.; Heathcock, C. H. J. Org. Chem. 1985, 50, 3247–3251; (b) Gray, B. D.; White, J. D. J. Chem. Soc., Chem. Commun. 1985, 20–21; (c) Sugano, Y.; Naruto, S. Chem. Pharm. Bull. 1989, 37, 840–842; (d) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961–1963; (e) Annunziata, R.; Cinquini, M.; Cozzi, F.; Borgia, A. L. J. Org. Chem. 1992, 57, 6339–6342; (f) Hattori, K.; Yamamoto, H. J. Org. Chem. 1993, 58, 5301–5303; (g) Enders, D. In Stereoselective Synthesis; Ottow, E.; Schöllkopf, K.; Schulz, B.-G., Eds.; Springer-Verlag: Berlin, 1993; pp. 63–90; (h) Boons, G.-J.; Downham, R.; Kim, K. S.; Ley, S. V.; Woods, M. Tetrahedron 1994, 50, 7157–7176; (i) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59–76; (j) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431–432.

4. For a recent review of chiral homoenolate equivalents: Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365–390. For a conceptually related synthon based on a dihydroxyacetone derivative, see: Enders, D.; Jegelka, U. Tetrahedron Lett. 1993, 34, 2453–2456.

5. Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way

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