Rapid Assembly of Molecular Complexity from Simple Enamides

Abstract

The efficient assembly of structurally complex molecules containing multiple continuous stereogenic centers still constitutes a tremendous challenge for any synthetic organic chemist. In this article, we briefly summarize our recent advances in the utilization of enamides as versatile building blocks for the rapid and highly stereoselective construction of different molecular scaffolds containing up to five continuous stereocenters.

Key words

stereoselective synthesis - enamides - tetrahydropyrans - domino reactions - molecular complexity

• References

• 1a Whitesides GM, Ismagilov RF. Science 1999; 284: 89
• 1b Nicolaou KC, Hale CR. H, Nilewski C, Ioannidou HA. Chem. Soc. Rev. 2012; 41: 5185
• 1c Nicolaou KC. Chem. Commun. 2003; 661
• 2a Caille S, Cui S, Faul MM, Mennen SM, Tedrow JS, Walker SD. J. Org. Chem. 2019; 84: 4583
• 2b Méndez-Lucio O, Medina-Franco JL. Drug Discovery Today 2017; 22: 120
• 3a Li J, Eastgate MD. Org. Biomol. Chem. 2015; 13: 7164
• 3b Mathematical and computational chemistry . Bonchev DG, Rouvray DH. Springer; New York: 2005
• 4a Eppe G, Didier D, Marek I. Chem. Rev. 2015; 115: 9175
• 4b Pellissier H. Chem. Rev. 2013; 113: 442
• 4c Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390
• 5a Bernadat G, Masson G. Synlett 2014; 25: 2842
• 5b Carbery DR. Org. Biomol. Chem. 2008; 6: 3455
• 5c Courant T, Dagousset G, Masson G. Synthesis 2015; 47: 1799
• 5d Gigant N, Chausset-Boissarie L, Gillaizeau I. Chemistry 2014; 20: 7548
• 5e Gopalaiah K, Kagan HB. Chem. Rev. 2011; 111: 4599
• 5f Matsubara R, Kobayashi S. Acc. Chem. Res. 2008; 41: 292
• 6 Halli J, Bolte M, Bats J, Manolikakes G. Org. Lett. 2017; 19: 674
• 7 Halli J, Kramer P, Grimmer J, Bolte M, Manolikakes G. J. Org. Chem. 2018; 83: 12007
• 8 Kramer P, Schönfeld J, Bolte M, Manolikakes G. Org. Lett. 2018; 20: 178
• 9 Matsubara R, Nakamura Y, Kobayashi S. Angew. Chem. Int. Ed. 2004; 43: 3258
• 10 Fossey JS, Matsubara R, Vital P, Kobayashi S. Org. Biomol. Chem. 2005; 3: 2910
• 11 Kramer P, Grimmer J, Bolte M, Manolikakes G. Angew. Chem. Int. Ed. 2019; 58: 13056
• 12a Nasir NM, Ermanis K, Clarke PA. Org. Biomol. Chem. 2014; 12: 3323
• 12b Vetica F, Chauhan P, Dochain S, Enders D. Chem. Soc. Rev. 2017; 46: 1661
• 12c Martín T, Padrón J, Martín V. Synlett 2013; 25: 12
• 12d Fuwa H. Mar. Drugs 2016; 14: 65
• 12e Larrosa I, Romea P, Urpí F. Tetrahedron 2008; 64: 2683