The upside of downsizing: Asymmetric trifunctional organocatalysts as small enzyme mimics for cooperative enhancement of both rate and enantioselectivity with regulation

Chirality

Volumn 25, Issue 11, 2013, Pages 675-683

  Liu, Fei ^a  

^a MACQUARIE UNIVERSITY   (Australia)

Author keywords

catalytic assembly; catalytic proficiency; enantioselective activation; multifunctional organocatalysts; organocatalysis regulation; proton transfer; REAP factor

Indexed keywords

MOLECULAR SCAFFOLD; PHOSPHONIUM DERIVATIVE; THIOUREA; TRANSITION ELEMENT;

ALDOL REACTION; ASYMMETRIC CATALYSIS; BIOCATALYSIS; CATALYST; CHIRALITY; CONTROLLED STUDY; CYCLOADDITION; DECELERATION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; EPOXIDATION; MICHAEL ADDITION; ORGANOCATALYST; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION TIME; REVIEW;

CATALYTIC ASSEMBLY; CATALYTIC PROFICIENCY; ENANTIOSELECTIVE ACTIVATION; MULTIFUNCTIONAL ORGANOCATALYSTS; ORGANOCATALYSIS REGULATION; PROTON TRANSFER; REAP FACTOR;

BIOMIMETIC MATERIALS; CATALYSIS; ENZYMES; KINETICS; ORGANIC CHEMICALS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84886639757     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22214     Document Type: Review

References (93)

1. Liebig J., Ueber die Bildung des Oxamids aus Cyan. Annalen der Chemie und Pharmacie 1860; 113: 246-247.
2. Knoevenagel E., Über Eine Darstellungsweise des Benzylidenacetessigesters. Ber Dtshe Chem Ges 1896; 29: 172-174.
3. Ostwald W., Die Fermente und ihre Wirkungen von C. Oppenheimer. Z Phys Chem 1900; 32: 509-511.
4. Bredig G, Fiske PS,. Durch Katalysatoren bewirkte Asymmetrische Synthese. Biochem Zeits 1912; 46: 7-23.
5. Dakin HD,. The catalytic action of amino-acids, peptones and proteins in effecting certain syntheses. J Biol Chem 1910; 7: 49-55.
6. Langenbeck W., Die organischen Katalysatoren und ihre Beziehungen zu den Fermenten. Berlin: Springer; 1935.
7. Langenbeck W, Borth G,. Über organische Katalysatoren, XXIV. Mitteil.: Aldolkondensation bei Gegenwart sekundärer Aminosäuren. Ber Dtshe Chem Ges 1942; 75: 951-953.
8. Pracejus H., Organische Katalysatoren, LXI. Asymmetrische Synthesen mit Ketenen, I. Alkaloid-katalysierte asymmetrische Synthesen von α-Phenyl-propionsäureestern. Justus Liebigs Ann Chem 1960; 634: 9-22.
9. Hajos ZG, Parrish DR,. Asymmetric synthesis of optically active polycyclic organic compounds. Ger Pat 1971:DE 2102623.
10. Eder U, Sauer G, Wiechert R,. Optically active 1,5-indanone and 1,6-naphthalenedione derivatives. Ger Pat 1971:DE 2014757.
11. Eder U, Sauer G, Wiechert R,. New type of asymmetric cyclization to optically active steroid CD partial structures. Angew Chem Int Ed Engl 1971; 10: 496-497.
12. Hajos ZG, Parrish DR,. Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J Org Chem 1974; 39: 1615-1621.
13. Långström B, Bergson G,. Asymmetric induction in a Michael-type reaction. Acta Chem Scand 1973; 27: 3118-3119.
14. Wynberg H, Helder R,. Asymmetric induction in the alkaloid-catalysed Michael reaction. Tetrahedron Lett 1975; 16: 4057-4060.
15. Hiemstra H, Wynberg H,. Addition of aromatic thiols to conjugated cycloalkenones, catalyzed by chiral β-hydroxy amines. A mechanistic study of homogeneous catalytic asymmetric synthesis. J Am Chem Soc 1981; 103: 417-430.
16. Wynberg H.,. Asymmetric catalysis by alkaloids. Top Stereochem 1986; 16: 87-129.
17. Dolling UH, Davis P, Grabowski EJJ,. Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalsysis. J Am Chem Soc 1984; 106: 446-447.
18. 2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins. J Am Chem Soc 1996; 118: 491-492.
19. Tu Y, Wang ZX, Shi Y,. An efficient catalytic asymmetric epoxidation method for trans-olefins mediated by a fructose-derived ketone. J Am Chem Soc 1996; 118: 9806-9807.
20. Juliá S, Masana J, Vega JC,. "Synthetic enzymes". Highly stereoselective epoxidation of chalcone in a triphasic toluene-water-poly[(S)- alanine] system. Angew Chem Int Ed Engl 1980; 19: 929-931.
21. Iyer MS, Gigstad KM, Namdev ND, Lipton M,. Asymmetric catalysis of the strecker amino acid synthesis by a cyclic dipeptide. J Am Chem Soc 1996; 118: 4910-4911.
22. Sigman MS, Jacobsen EN,. Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries. J Am Chem Soc 1998; 120: 4901-4902.
23. Corey EJ, Grogan MJ,. Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst. Org Lett 1999; 1: 157-160.
24. Miller SJ, Copeland GT, Papaioannou N, Horstmann TE, Ruel EM,. Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure. J Am Chem Soc 1998; 120: 1629-1630.
25. Iwabuchi Y, Nakatani M, Yokoyama N, Hatakeyama S,. Chiral amine-catalyzed asymmetric Baylis-Hillman reaction. J Am Chem Soc 1999; 121:10219- 10220.
26. Copeland RA,. A brief history of enzymology. In: Enzymes: a practical introduction to structure, mechanism, and data analysis, 2nd ed. New York: John Wiley & Sons; 2000. p 1-10.
27. Keinan E, editor. Catalytic antibodies. New York: John Wiley & Sons; 2005.
28. Wagner J, Lerner RA, Barbas ICF,. Efficient aldolase catalytic antibodies that use the enamine mechanism of natural enzymes. Science 1995; 270: 1797-1800.
29. List B, Lerner RA, Barbas CF,. Proline-catalyzed direct asymmetric aldol reactions. J Am Chem Soc 2000; 122: 2395-2396.
30. Ahrendt KA, Borths CJ, MacMillan DWC,. New strategies for organic catalysis: the first highly enantioselective organocatalytic Diels-Alder reaction. J Am Chem Soc 2000; 122: 4243-4244.
31. Dalko PI, Moisan L,. In the golden age of organocatalysis. Angew Chem Int Ed Engl 2004; 43: 5138-5175.
32. List B, Maruoka K,. Asymmetric organocatalysis-workbench edition. New York: Georg Thieme Verlag; 2012.
33. List B, editor. Asymmetric organocatalysis. Topics in current chemistry. Verlag Berlin Heidelberg: Springer; 2009; vol. 291.
34. Dalko PI, editor. Enantioselective organocatalysis: reactions and experimental procedures. New York: Wiley-VCH; 2007.
35. Berkessel A, Gröger H,. Asymmetric organocatalysis: from biomimetic concepts to applications in asymmetric synthesis, 1st ed. New York: Wiley-VCH; 2005.
36. Dondoni A, Massi A,. Asymmetric organocatalysis: from infancy to adolescence. Angew Chem Int Ed Engl 2008; 47: 4638-4660.
37. Waser M,. Asymmetric organocatalysis in natural product syntheses. Progress in the chemistry of organic natural products. Verlag Wien: Springer; 2012; vol. 96.
38. Garcia-Viloca M, Gao J, Karplus M, Truhlar DG,. How enzymes work: analysis by modern rate theory and computer simulations. Science 2004; 303: 186-195.
39. Cheng AA, Lu TK,. Synthetic biology: an emerging engineering discipline. Annu Rev Biomed Eng 2012; 14: 155-178.
40. Cherry JR, Fidantsef AL,. Directed evolution of industrial enzymes: an update. Curr Opin Biotechnol 2003; 14: 438-443.
41. Farinas ET, Bulter T, Arnold FH,. Directed enzyme evolution. Curr Opin Biotechnol 2001; 12: 545-551.
42. Brunner H,. Optically active organometeallic compounds of transition elements with chiral metal atoms. Angew Chem Int Ed Engl 1999; 38: 1194-1208.
43. Beller M, Bolm C,. Transition metals for organic synthesis. 2nd ed. New York: Wiley-VCH; 2004.
44. Sheldon RA, Arends I, Hanefeld U,. Green chemistry and catalysis. New York: Wiley-VCH; 2007.
45. Bock DA, Lehmann CW, List B,. Crystal structures of proline-derived enamines. Proc Natl Acad Sci U S A 2010; 107:20636- 20641.
46. Saito S, Yamamoto H,. Design of acid-base catalysis for the asymmetric direct aldol reaction. Acc Chem Res 2004; 37: 570-579.
47. List B, Hoang L, Martin HJ,. New mechanistic studies on the proline-catalyzed aldol reaction. Proc Natl Acad Sci U S A 2004; 101: 5839-5842.
48. Jacobsen EN, MacMillan DWC,. From the Cover: Organocatalysis Special Feature: Organocatalysis. Proc Natl Acad Sci U S A 2010; 107:20618- 20619.
49. Giacalone F, Gruttadauria M, Agrigento P, Noto R,. Low-loading asymmetric organocatalysis. Chem Soc Rev 2012; 41: 2406-2447.
50. Sigman MS, Vachal P, Jacobsen EN,. A general catalyst for the asymmetric Strecker reaction. Angew Chem Int Ed Engl 2000; 39: 1279-1281.
51. Lichtor PA, Miller SJ,. Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation. Nat Chem 2012; 4: 990-995.
52. Davie EAC, Mennen SM, Xu Y, Miller SJ,. Asymmetric catalysis mediated by synthetic peptides. Chem Rev 2007; 107: 5759-5812.
53. Huang Y, Unni AK, Thadani AN, Rawal VH,. Hydrogen bonding: single enantiomers from a chiral-alcohol catalyst. Nature 2003; 424: 146-146.
54. Wang J, Xie H, Li H, Zu L, Wang W,. A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution. Angew Chem Int Ed Engl 2008; 47: 4177-4179.
55. Shirakawa S, Kasai A, Tokuda T, Maruoka K,. Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions. Chem Sci 2013; 4: 2248.
56. Richard JP,. A paradigm for enzyme-catalyzed proton transfer at carbon: triosephosphate isomerase. Biochemistry 2012; 51: 2652-2661.
57. Wolfenden R, Snider MJ,. The depth of chemical time and the power of enzymes as catalysts. Acc Chem Res 2001; 34: 938-945.
58. Alber T, Banner DW, Bloomer AC, Petsko GA, Phillips D, Rivers PS, Wilson IA,. On the three-dimensional structure and catalytic mechanism of triosephosphate isomerase. Phil Trans R Soc Lond B Biol Sci 1981; 293: 159-171.
59. Wolfenden R, Radzicka A,. A proficient enzyme. Science 1995; 267: 90-93.
60. Knowles JR, Albery JW,. Perfection in enzyme catalysis: the energertics of triosephosphate isomerase. Acc Chem Res 1977; 10: 105-111.
61. Miller BG, Hassell AM, Wolfenden R, Milburn MV, Short SA,. Anatomy of a proficient enzyme: the structure of orotidine 5'-monophosphate decarboxylase in the presence and absence of a potential transition state analog. Proc Natl Acad Sci U S A 2000; 97: 2011-2016.
62. Xu H, Zuend SJ, Woll MG, Tao Y, Jacobsen EN,. Asymmetric cooperative catalysis of strong bronsted acid-promoted reactions using chiral ureas. Science 2010; 327: 986-990.
63. Seayad J, List B,. Asymmetric organocatalysis. Org Biomol Chem 2005; 3: 719-724.
64. Wang C-J, Zhang Z-H, Dong X-Q, Wu X-J,. Chiral amine-thioureas bearing multiple hydrogen bonding donors: highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins. Chem Commun 2008; 1431-1433.
65. Wende RC, Schreiner PR,. Evolution of asymmetric organocatalysis: multi- and retrocatalysis. Green Chem 2012; 14: 1821-1849.
66. Huang Y, Walji AM, Larsen CH, MacMillan DWC,. Enantioselective organo-cascade catalysis. J Am Chem Soc 2005; 127:15051- 15053.
67. Chen W, Du W, Duan Y-Z, Wu Y, Yang S-Y, Chen Y-C,. Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: beneficial effects of hydrogen bonding. Angew Chem Int Ed Engl 2007; 46: 7667-7670.
68. Ema T, Tanida D, Matsukawa T, Sakai T,. Biomimetic trifunctional organocatalyst showing a great acceleration for the transesterification between vinyl ester and alcohol. Chem Commun 2008; 957-959.
69. Anstiss C, Liu F,. Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts. Tetrahedron 2010; 66: 5486-5491.
70. Garnier J-M, Liu F,. Trifunctional organocatalyst-promoted counterion catalysis for fast and enantioselective aza-Morita-Baylis-Hillman reactions at ambient temperature. Org Biomol Chem 2009; 7: 1272-1275.
71. Garnier J-M, Anstiss C, Liu F,. Enantioselective trifunctional organocatalysts for rate- enhanced aza-Morita-Baylis-Hillman reactions at room temperature. Adv Synth Catal 2009; 351: 331-338.
72. Santos LS, Pavam CH, Almeida WP, Coelho F, Eberlin MN,. Probing the mechanism of the Baylis-Hillman reaction by electrospray ionization mass and tandem mass spectrometry. Angew Chem Int Ed Engl 2004; 116: 4430-4433.
73. Raheem IT, Jacobsen EN,. Highly Enantioselective aza-Baylis-Hillman reactions catalyzed by chiral thiourea derivatives. Adv Synth Catal 2005; 347: 1701-1708.
74. Aggarwal VK, Fulford SY, Lloyd-Jones GC,. Reevaluation of the mechanism of the Baylis-Hillman reaction: implications for asymmetric catalysis. Angew Chem Int Ed Engl 2005; 44: 1706-1708.
75. Price KE, Broadwater SJ, Jung HM, McQuade DT,. Baylis-Hillman mechanism: a new interpretation in aprotic solvents. Org Lett 2005; 7: 147-150.
76. Price KE, Broadwater SJ, Walker BJ, McQuade DT,. A new interpretation of the Baylis-Hillman mechanism. J Org Chem 2005; 70: 3980-3987.
77. Buskens P, Klankermayer J, Leitner W,. Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman mechanism. J Am Chem Soc 2005; 127:16762- 16763.
78. Robiette R, Aggarwal VK, Harvey JN,. Mechanism of the Morita-Baylis-Hillman reaction: a computational investigation. J Am Chem Soc 2007; 129:15513- 15525.
79. Wei Y, Shi M,. Multifunctional chiral phosphine organocatalysis in catalytic asymmetric Morita-Baylis-Hillman and related reactions. Acc Chem Res 2010; 43: 1005-1018.
80. Lindner C, Liu Y, Karaghiosoff K, Maryasin B, Zipse H,. The aza-morita-baylis-hillman reaction: a mechanistic and kinetic study. Chem Eur J 2013; 19: 6429-6434.
81. Bjelic S, Nivon LG, Celebi-Olcum N, et al. Computational design of enone-binding proteins with catalytic activity for the morita-baylis-hillman reaction. ACS Chem Biol 2013; 8: 749-757.
82. Perry FA, Hegeman AD,. Enzymatic reaction mechanisms, 1st ed. Oxford, UK: Oxford University Press; 2007.
83. MacMillan DW,. The advent and development of organocatalysis. Nature 2008; 455: 304-308.
84. Hammes GG,. How do enzymes really work? J Biol Chem 2008; 283:22337- 22346.
85. Hammes GG,. Multiple conformational changes in enzyme catalysis. Biochemistry 2002; 41: 8221-8228.
86. Walsh CT,. The chemical versatility of natural-product assembly lines. Acc Chem Res 2008; 41: 4-10.
87. Movassaghi M, Jacobsen EN,. The simplest «enzyme.» Science 2002; 298: 1904-1905.
88. Pellissier H,. Recent developments in asymmetric organocatalytic domino reactions. Cambridge, UK: RSC Publishing; 2010.
89. de Graaff C, Ruijter E, Orru RVA,. Recent developments in asymmetric multicomponent reactions. Chem Soc Rev 2012; 41: 3969-4009.
90. Bernardi L, Fochi M, Comes Franchini M, Ricci A,. Bioinspired organocatalytic asymmetric reactions. Org Biol Chem 2012; 10: 2911-2922.
91. Meeuwissen J, Reek JNH,. Supramolecular catalysis beyond enzyme mimics. Nat Chem 2010; 2: 615-621.
92. Wiester MJ, Ulmann PA, Mirkin CA,. Enzyme mimics based upon supramolecular coordination chemistry. Angew Chem Int Ed Engl 2011; 50: 114-137.
93. Enders D, Huttl MR, Grondal C, Raabe G,. Control of four stereocentres in a triple cascade organocatalytic reaction. Nature 2006; 441: 861-863.