RSS-Feed abonnieren
DOI: 10.1055/s-0030-1260607
Catalytic Decarboxylative Reactions: Biomimetic Approaches Inspired by Polyketide Biosynthesis
Publikationsverlauf
Publikationsdatum:
26. Mai 2011 (online)
Abstract
This short review summarizes decarboxylative reactions of malonic acid half thio/oxyester mediated by metal complexes and organocatalysts. These biomimetic reactions are inspired by similar reactions catalyzed by polyketide synthase. While they have been known for several decades, this is the first review of these reactions.
1 Introduction
2 Decarboxylative Reactions Catalyzed by Metal Complexes
2.1 Condensation Reaction
2.2 Aldol Reaction
2.3 1,4-Addition
3 Organocatalytic Decarboxylative Reactions
3.1 Condensation Reaction
3.2 Aldol Reaction
3.3 1,4-Addition
3.4 Mannich Reaction
3.5 Amination Reaction
3.6 Protonation
4 Conclusion
Key words
decarboxylative reactions - organocatalytic reactions - malonic acid half thioester - asymmetric catalysis - enantioselectivity
-
1a
O’Hagan D. The Polyketide Metabolites Ellis Horwood; Chichester: 1991. -
1b
Heath RJ.Rock RO. Nat. Prod. Rep. 2002, 19: 581 -
1c
Austin MB.Izumikawa M.Bowman ME.Udwary DW.Ferrer J.-L.Moore BS.Noel JP. J. Biol. Chem. 2004, 279: 45162 - 2
Kobuke Y.Yoshida J.-i. Tetrahedron Lett. 1978, 19: 367 - 3
Sakai M.Sordé N.Matile S. Molecules 2001, 6: 845 - 4
Berrué F.Antoniotti S.Thomas OP.Amade P. Eur. J. Org. Chem. 2007, 1743 -
5a
Machajewski TD.Wong C.-H. Angew. Chem. Int. Ed. 2000, 39: 1352 -
5b
Palomo C.Oiarbide M.Garcia JM. Chem. Soc. Rev. 2004, 33: 65 -
5c
Schetter B.Mahrwald R. Angew. Chem. Int. Ed. 2006, 45: 7506 - 6
Lalic G.Aloise AD.Shair MD. J. Am. Chem. Soc. 2003, 125: 2852 -
7a
Orlandi S.Benaglia M.Cozzi F. Tetrahedron Lett. 2004, 45: 1747 -
7b
Magdziak D.Lalic G.Lee HM.Fortner KC.Aloise AD.Shair MD. J. Am. Chem. Soc. 2005, 127: 7284 - 8
Fortner KC.Shair MD. J. Am. Chem. Soc. 2007, 129: 1032 - 9
Sibi MP.Manyem S. Tetrahedron 2000, 56: 8033 - 10
Furutachi M.Mouri S.Matsunaga S.Shibasaki M. Chem. Asian J. 2010, 5: 2351 -
11a
Bordwell FG.Fried HE. J. Org. Chem. 1981, 46: 4327 -
11b
Bordwell FG.Fried HE. J. Org. Chem. 1991, 56: 4218 - 12
Ryu Y.Scott AI. Tetrahedron Lett. 2003, 44: 7499 - 13
List B.Doehring A.Fonseca M.Wobser K.van Thienen H.Torres R.Galilea P. Adv. Synth. Catal. 2005, 347: 1558 - 14
Blaquiere N.Shore DG.Rousseaux S.Fagnou K. J. Org. Chem. 2009, 74: 6190 - 15
Lubkoll J.Wennemers H. Angew. Chem. Int. Ed. 2007, 46: 6841 -
16a
Enantioselective Synthesis of β-Amino
Acids
2nd ed.:
Juaristi E.Soloshonok VA. Wiley; Hoboken: 2005. -
16b
Liu M.Sibi MP. Tetrahedron 2002, 58: 7991 -
17a
Ting A.Schaus SE. Eur. J. Org. Chem. 2007, 5797 -
17b
Verkade JMM.van Hermert LJC.Quaedflieg PJLM.Rutjes FPJT. Chem. Soc. Rev. 2008, 37: 29 - 18
Ricci A.Petterson D.Bernardi L.Fini F.Fochi M.Perez Herrera R.Sgarzani V. Adv. Synth. Catal. 2007, 349: 1037 - 19
Banchet J.Lefebvre P.Legay R.Lasne M.-A.Rouden J. Green Chem. 2010, 12: 252 -
20a
Jiang Z.Pan Y.Zhao Y.Ma T.Lee R.Yang Y.Huang K.-W.Wong MW.Tan C.-H. Angew. Chem. Int. Ed. 2009, 48: 3627 -
20b
Lee R.Lim X.Chen T.Tan G.Tan C.-H.Huang K.-W. Tetrahedron Lett. 2009, 50: 1560 -
21a
Leow D.Tan C.-H. Chem. Asian J. 2009, 4: 488 -
21b
Leow D.Tan C.-H. Synlett 2010, 1589 - 22
Pan Y.Kee CW.Jiang Z.Ma T.Zhao Y.Yang Y.Xue H.Tan C.-H. Chem. Eur. J. 2011, accepted -
23a
Fehr C. Angew. Chem. Int. Ed. 1996, 35: 2566 -
23b
Duhamel L.Duhamel P.Plaquevent J.-C. Tetrahedron: Asymmetry 2004, 15: 3653 - 24
Brunner H.Müller J.Spitzer J. Monatsh. Chem. 1996, 127: 845 - 25
Banchet J.Baudoux J.Amere M.Lasne M.-A.Rouden J. Eur. J. Org. Chem. 2008, 5493 - 26
Toussaint O.Capdevielle P.Maumy M. Tetrahedron Lett. 1987, 28: 539 - 27
Brunner H.Kurzwart M. Monatsh. Chem. 1992, 123: 121 - 28
Brunner H.Baur MA. Eur. J. Org. Chem. 2003, 2854 -
29a
Rogers LM.-A.Rouden J.Lecomte L.Lasne M.-C. Tetrahedron Lett. 2003, 44: 3047 -
29b
Seitz T.Baudoux J.Bekolo H.Cahard D.Plaquevent J.-C.Lasne M.-C.Rouden J. Tetrahedron 2006, 62: 6155 -
29c
Amere M.Lasne M.-C.Rouden J. Org. Lett. 2007, 9: 2621 -
30a
Marckwald W. Ber. Dtsch. Chem. Ges. 1904, 37: 349 -
30b
Marckwald W. Ber. Dtsch. Chem. Ges. 1904, 37: 1368