5-Alkyl and 5,5-Dialkyl Meldrum’s Acids

Introduction

5-Alkyl and 5,5-dialkyl Meldrum’s acids (1 and 2, respectively) are used in total synthesis.[1] Monoalkylated derivatives 1 are synthesized from Meldrum’s acid 3 by condensation with aldehyde[2] (or by acylation[3]) followed by hydrogenation.

5,5-Dialkyl Meldrum’s acids 2 can be obtained by alkylation of Meldrum’s acid 3 or its monoalkylated derivatives 1 (Scheme [1]).[4] Herein, reactions of Meldrum’s acids 1 and 2 proceeding with destruction of 1,3-dioxane cycle are reviewed.

Scheme 1

• References

• 1 Ivanov AS. Chem. Soc. Rev. 2008; 37: 789
• 2 Tóth G, Kövér KE. Synth. Commun. 1995; 3067
• 3 Nutaitis CF, Schultz RA, Obaza J, Smith FX. J. Org. Chem. 1980; 45: 4606
• 4 Chan C.-C, Huang X. Synthesis 1982; 452
• 5a Scheuer PJ, Cohen SG. J. Am. Chem. Soc. 1958; 80: 4933
• 5b Jacobs RT, Wright AD, Smith FX. J. Org. Chem. 1982; 47: 3769
• 6 Collins KD, Oliveira JM, Guazzelli G, Sautier B, De Grazia S, Matsubara H, Helliwell M, Procter DJ. Chem.–Eur. J. 2010; 16: 10240
• 7 Detz RJ, Abiri Z, le Griel R, Hiemstra H, van Maarseveen JH. Chem.–Eur. J. 2011; 17: 5921
• 8 Frost CG, Hartley BC. J. Org. Chem. 2009; 74: 3599
• 9 Frost CG, Penrose SD, Gleave R. Synthesis 2009; 627
• 10 Sautier B, Lyons SE, Webb MR, Procter DJ. Org. Lett. 2012; 14: 146
• 11 Wilsily A, Nguyen Y, Fillion E. J. Am. Chem. Soc. 2009; 131: 15606
• 12 Mahoney SJ, Lou T, Bondarenko G, Fillion E. Org. Lett. 2012; 14: 3474
• 13 Krabbe SW, Do DT, Johnson JS. Org. Lett. 2012; 14: 5932
• 14 Akué-Gédu R, Hénichart J.-P, Couturier D, Rigo B. Tetrahedron Lett. 2004; 45: 9197
• 15 Li S, Jia W, Jiao N. Adv. Synth. Catal. 2009; 351: 569
• 16 Jia W, Li S, Yu M, Chen W, Jiao N. Tetrahedron Lett. 2009; 50: 5406
• 17a Dardennes E, Kovács-Kulyassa Á, Renzetti A, Sapi J, Laronze J.-Y. Tetrahedron Lett. 2003; 44: 221
• 17b Dardennes E, Kovács-Kulyassa Á, Boisbrun M, Petermann C, Laronze J.-Y, Sapi J. Tetrahedron: Asymmetry 2005; 16: 1329
• 17c Dardennes E, Gérard S, Petermann C, Sapi J. Tetrahedron: Asymmetry 2010; 21: 208