Organocatalytic enantioselective protonation of enol derivatives

Mini-Reviews in Organic Chemistry

Volumn 11, Issue 4, 2014, Pages 410-423

  Leow, Dasheng ^a   Shen, Juan ^b   Su, Ying ^a   Peh, Guangrong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Enantioselective protonation; Enolates and enols; Organocatalysis

Indexed keywords

ENANTIOSELECTIVITY; PROTONATION;

ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE; ENANTIOSELECTIVE PROTONATION; ENOLATE AND ENOL; ENOLATES; ORGANIC SYNTHESIS; ORGANOCATALYSIS; ORGANOCATALYSTS; ORGANOCATALYTIC; PROTONATIONS;

OLEFINS;

EID: 84911368129     PISSN: 1570193X     EISSN: 18756298     Source Type: Journal    
DOI: 10.2174/1570193x1104140926165654     Document Type: Article

References (80)

1. Rouden, J. In Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis. Choong, E.S., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2009, pp. 171-196.
2. For reviews on enantioselective protonation reactions, see: Fehr, C. Enantioselective protonation of enolates and enols. Angew. Chem. Int. Ed. Engl., 1996, 35, 2566-2587
3. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Asymmetric protonations of enol derivatives. Synlett, 1997, 411-420
4. Eames, J.; Weerasooriya, N. Recent advances into the enantioselective protonation of prostereogenic enol derivatives. Tetrahedron: Asymmetry, 2001, 12, 1-24
5. Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Enantioselective protonations: fundamental insights and new concepts. Tetrahedron: Asymmetry, 2004, 15, 3653-3691
6. Mohr, J.T.; Hong, A.Y.; Stoltz, B.M. Enantioselective protonation. Nat. Chem., 2009, 1, 359-369
7. Claraz, A.; Oudeyer, S.; Levacher, V. Deracemization of α-substituted carbonyl compounds via catalytic enantioselective protonation of their corresponding enolates. Curr. Org. Chem., 2012, 16, 2192-2205.
8. Piva, O.; Pete, J.-P. Highly enantioselective protonation of photodienols an unusual substituent effect on the induced chirality. Tetrahedron Lett., 1990, 31, 5157-5160
9. Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J.-P. Highly enantioselective photodeconjugation of α,β-unsaturated esters. Origin of the chiral discrimination. J. Am. Chem. Soc., 1990, 112, 9263-9272.
10. Duhamel, L.; Plaquevent, J.-C. Deracemisation par protonation enantioselective. Tetrahedron Lett., 1977, 18, 2285-2288
11. Henze, R.; Duhamel, L.; Lasne, M.-C. Enantioselective tautomerization of a new metastable enol. Tetrahedron: Asymmetry, 1997, 8, 3363-3365.
12. Duhamel, L.; Launay, J.-C. Enantioselectivity in enediolhydroxyketone tautomerization. Tetrahedron Lett., 1983, 24, 4209-4212
13. Zhao, Y.; Lim, X.; Pan, Y.; Zong, L.; Feng, W.; Tan, C. H.; Huang, K.-W. Asymmetric H-D exchange reactions of fluorinated aromatic ketones. Chem. Commun., 2012, 48, 5479-5481.
14. Lee, J.-W.; List, B. Deracemization of α-aryl hydrocoumarins via catalytic asymmetric protonation of ketene dithioacetals. J. Am. Chem. Soc., 2012, 134, 18245-18248.
15. Kim, B.M.; Kim, H.; Kim, W.; Im, K.Y.; Park, J.K. Asymmetric protonation of ketone enolates using chiral β-hydroxyethers: acidity-tuned enantioselectivity. J. Org. Chem., 2004, 69, 5104-5107
16. Mitsuhashi, K.; Ito, R.; Arai, T.; Yanagisawa, A. Catalytic asymmetric protonation of lithium enolates using amino acid derivatives as chiral proton sources. Org. Lett., 2006, 8, 1721-1724.
17. Ishihara, K.; Kaneeda, M.; Yamamoto, H. Lewis Acid Assisted chiral Brønsted acid for enantioselective protonation of silyl enol ethers and ketene bis(trialkylsilyl) acetals. J. Am. Chem. Soc., 1994, 116, 11179-11180
18. Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. First example of a highly enantioselective catalytic protonation of silyl enol ethers using a novel Lewis acid-assisted Brønsted acid system. J. Am. Chem. Soc., 1996, 118, 12854-12855.
19. Cheon, C.H.; Yamamoto, H. A Brønsted acid catalyst for the enantioselective protonation reaction. J. Am. Chem. Soc., 2008, 130, 9246-9247.
20. Poisson, T.; Dalla, V.; Marsais, F.; Dupas, G.; Oudeyer, S.; Levacher, V. Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF. Angew. Chem. Int. Ed. Engl., 2007, 46, 7090-7093
21. Poisson, T.; Gembus, V.; Dalla, V.; Oudeyer, S.; Levacher, V. Organocatalyzed enantioselective protonation of silyl enol ethers: scope, limitations, and application to the preparation of enantioenriched homoisoflavones. J. Org. Chem., 2010, 75, 7704-7716.
22. Poisson, T.; Oudeyer, S.; Dalla, V.; Marsais, F.; Levacher, V. Straightforward organocatalytic enantioselective protonation of silyl enolates by means of cinchona alkaloids and carboxylic acids. Synlett, 2008, 2447-2450.
23. Uraguchi, D.; Kinoshita, N.; Ooi, T. Catalytic asymmetric protonation of α-amino acid-derived ketene disilyl acetals using P-spiro diaminodioxaphosphonium barfates as chiral proton. J. Am. Chem. Soc., 2010, 132, 12240-12242.
24. Yamamoto, E.; Nagai, A.; Hamasaki, A.; Tokunaga, M. Catalytic asymmetric hydrolysis: asymmetric hydrolytic protonation of enol esters catalyzed by phase-transfer catalysts. Chem. Eur. J., 2011, 17, 7178-7182
25. Yamamoto, E.; Gokuden, D.; Nagai, A.; Kamachi, T.; Yoshizawa, K.; Hamasaki, A.; Ishida, T.; Tokunaga, M. Hydrolytic enantioselective protonation of cyclic dienyl esters and a β‑diketone with chiral phase-transfer catalysts. Org. Lett., 2012, 14, 6178-6181.
26. Claraz, A.; Leroy, J.; Oudeyer, S.; Levacher, V. Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids. J. Org. Chem., 2011, 76, 6457-6463.
27. Beck, E.M.; Hyde, A.M.; Jacobsen, E.N. Chiral sulfinamide/achiral sulfonic acid cocatalyzed enantioselective protonation of enol silanes. Org. Lett., 2011, 13, 4260-4263.
28. Guin, J.; Varseev, G.; List, B. Catalytic asymmetric protonation of silyl ketene imines. J. Am. Chem. Soc., 2013, 135, 2100-2103.
29. Paull, D.H.; Weatherwax, A.; Lectka, T. Catalytic, asymmetric reactions of ketenes and ketene enolates. Tetrahedron, 2009, 65, 6771-6803.
30. Pracejus, H. Alkaloid-katalysierte asymmetrische synthesen von α-phenyl-propionsäureestern. Justus Liebigs Ann. Chem., 1960, 634, 9-22
31. Pracejus, H.; Mätje, H. Zusammenhänge zwischen dem räumlichen bau einiger alkaloidartiger katalysatoren und ihren stereospezifischen wirkungen bei asymmetrischen Estersynthesen. J. Prakt. Chem., 1964, 24, 195-205.
32. Fehr, C.; Stempf, I.; Galindo, J. Enantioselective addition of aromatic thiols to a ketene. Angew. Chem. Int. Ed. Engl., 1993, 32, 1044-1046.
33. Hodous, B.L.; Ruble, J.C.; Fu, G.C. Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: catalytic asymmetric synthesis of arylpropionic acids. J. Am. Chem. Soc., 1999, 121, 2637-2638
34. Wiskur, S.L.; Fu, G.C. Catalytic asymmetric synthesis of esters from ketenes. J. Am. Chem. Soc., 2005, 127, 6176-6177.
35. Hodous, B.L.; Fu, G.C. Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: possible intervention of chiral Brønsted-acid catalysis. J. Am. Chem. Soc., 2002, 124, 10006-10007
36. Pattawong, O.; Mustard, T.J.L.; Johnston, R.C.; Cheong, P.H.-Y. Mechanism and stereocontrol: enantioselective addition of pyrrole to ketenes using planar-chiral organocatalysts. Angew. Chem. Int. Ed. Engl., 2013, 52, 1420-1423.
37. Schaefer, C.; Fu, G.C. Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters. Angew. Chem. Int. Ed. Engl., 2005, 44, 4606-4608.
38. Dai, X.; Nakai, T.; Romero, J.A.C.; Fu, G.C. Enantioselective synthesis of protected amines by the catalytic asymmetric addition of hydrazoic acid to ketenes. Angew. Chem. Int. Ed. Engl., 2007, 46, 4367-4369.
39. Nair, V.; Menon, R.S.; Biju, A.T.; Sinu, C.R.; Paul, R.R.; Jose, A.; Sreekumar, V. Employing homoenolates generated by NHC catalysis in carbon-carbon bond-forming reactions: state of the art. Chem. Soc. Rev., 2011, 40, 5336-5346
40. Bugaut, X.; Glorius, F. Organocatalytic umpolung: N-heterocyclic carbenes and beyond. Chem. Soc. Rev., 2012, 41, 3511-3522
41. Vora, H.U.; Wheeler, P.; Rovis, T. Exploiting acyl and enol azolium intermediates via Nheterocyclic carbene-catalyzed reactions of α-reducible aldehydes. Adv. Synth. Catal., 2012, 354, 1617-1639.
42. Reynolds, N.T.; Rovis, T. Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloroesters. J. Am. Chem. Soc., 2005, 127, 16406-16407.
43. Vora, H.U.; Rovis, T. N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of α-protio and α-deuterio α-chloro and α-fluoro carboxylic acids. J. Am. Chem. Soc., 2010, 132, 2860-2861.
44. Maki, B.E.; Chan, A.; Scheidt, K.A. Protonation of homoenolate equivalents generated by N-heterocyclic carbenes. Synthesis, 2008, 1306-1315
45. Maki, B.E.; Patterson, E.V.; Cramer, C.J.; Scheidt, K.A. Impact of solvent polarity on N-heterocyclic carbenecatalyzed β-protonations of homoenolate equivalents. Org. Lett., 2009, 11, 3942-3945.
46. Pracejus, H.; Wilcke, F.-W.; Hanemann, K. Asymmetrisch katalysierte additionen von thiolen an α-aminoacrylsäurederivate und nitroolefine. J. Prakt. Chem., 1977, 319, 219-229.
47. Kumar, A.; Salunkhe, R.V.; Rane, R.A.; Dike, S.Y. Novel catalytic enantioselective protonation (proton transfer) in Michael addition of benzenethiol to α-acrylacrylates: synthesis of (S)-naproxen and α-arylpropionic acids or esters. J. Chem. Soc. Chem. Commun., 1991, 485-486.
48. Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts. Synlett, 2005, 603-606.
49. Wang, Y.; Liu, X.; Deng, L. Dual-function cinchona alkaloid catalysis: catalytic asymmetric tandem conjugate additionprotonation for the direct creation of nonadjacent stereocenters. J. Am. Chem. Soc., 2006, 128, 3928-3930
50. Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. Control of diastereoselectivity in tandem asymmetric reactions generating nonadjacent stereocenters with bifunctional catalysis by cinchona alkaloids. J. Am. Chem. Soc., 2007, 129, 768-769.
51. Ishikawa, T.; Kumamoto, T. Guanidines in organic synthesis. Synthesis, 2006, 737-752
52. Leow, D.; Tan, C.-H. Chiral guanidine catalyzed enantioselective reactions. Chem. Asian J., 2009, 4, 488-507
53. Leow, D.; Tan, C.-H. Catalytic reactions of chiral guanidines and guanidinium salts. Synlett, 2010, 1589-1605
54. Selig, P. Guanidine organocatalysis. Synthesis, 2013, 703-718.
55. Leow, D.; Lin, S.; Chittimalla, S.K.; Fu, X.; Tan, C.-H. Enantioselective protonation catalyzed by a chiral bicyclic guanidine derivative. Angew. Chem. Int. Ed. Engl., 2008, 47, 5641-5645
56. Cho, B.; Tan, C.-H.; Wong, M.W. Origin of asymmetric induction in bicyclic guanidine-catalyzed thio-Michael reaction: a bifunctional mode of Lewis acid-Brønsted acid activation. J. Org. Chem., 2012, 77, 6553-6562.
57. Lin, S.; Leow, D.; Huang, K.-W.; Tan, C.-H. Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond. Chem. Asian J., 2009, 4, 1741-1744.
58. Lu, M.; Zhu, D.; Lu, Y.; Hou, Y.; Tan, B.; Zhong, G. Organocatalytic asymmetric α-aminoxylation/aza-Michael reactions for the synthesis of functionalized tetrahydro-1,2-oxazines. Angew. Chem. Int. Ed. Engl., 2008, 47, 10187-10191.
59. Jousseaume, T.; Wurz, N.E.; Glorius, F. Highly enantioselective synthesis of α-amino acid derivatives by an NHC-catalyzed intermolecular Stetter reaction. Angew. Chem. Int. Ed. Engl., 2011, 50, 1410-1414.
60. Duan, S.-W.; An, J.; Chen, J.-R.; Xiao, W.-J. Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade. Org. Lett., 2011, 13, 2290-2293.
61. Rueping, M.; Theissmann, T.; Raja, S.; Bats, J.W. Asymmetric counterion pair catalysis: an enantioselective Brønsted acidcatalyzed protonation. Adv. Synth. Catal., 2008, 350, 1001-1006
62. Fu, N.; Zhang, L.; Li, J.; Luo, S.; Cheng, J.-P. Chiral primary amine catalyzed enantioselective protonation via an enamine intermediate. Angew. Chem. Int. Ed. Engl., 2011, 50, 11451-11455.
63. Dai, L.; Yang, H.; Niu, J.; Chen, F.-E. Enantioselective protonation in the sulfa-Michael addition using chiral squaramides as hydrogen-bonding organocatalysts. Synlett, 2012, 314-316.
64. Rana, N.K.; Singh, V.K. Enantioselective enolate protonation in sulfa-Michael addition to α-substituted N-acryloyloxazolidin-2-ones with bifunctional organocatalyst. Org. Lett., 2011, 13, 6520-6523
65. Unhale, R.A.; Rana, N.K.; Singh, V.K. Organocatalytic enantioselective transient enolate protonation in conjugate addition of thioacetic acid to α-substituted N-acryloyloxazolidinones. Tetrahedron Lett., 2013, 54, 1911-1915.
66. Kimmel, K.L.; Weaver, J.D.; Lee, M.; Ellman, J.A. Enantioselective enolate protonation in sulfa-Michael addition to α-substituted N-acryloyloxazolidin-2-ones with bifunctional organocatalyst. J. Am. Chem. Soc., 2012, 134, 9058-9061.
67. Rueping, M.; Ieawsuwan, W.; Antonchick, A.P.; Nachtsheim, B.J. Chiral Brønsted acids in the catalytic asymmetric Nazarov cyclization-the first enantioselective organocatalytic electrocyclic reaction. Angew. Chem. Int. Ed. Engl., 2007, 46, 2097-2100
68. Rueping, M.; Ieawsuwan, W. A catalytic asymmetric electrocyclization-protonation reaction. Adv. Synth. Catal., 2009, 351, 78-84.
69. Capitta, F.; Frongia, A.; Piras, P.P.; Pitzanti, P.; Secci, F. Enantioselective organocatalytic rearrangement of α-acyloxy-β-keto sulfides to α-acyloxy thioesters. Adv. Synth. Catal., 2010, 352, 2955-2960
70. Capitta, F.; Frongia, A.; Piras, P.P.; Pitzanti, P.; Secci, F. Organocatalytic asymmetric tandem condensation-intramolecular rearrangement-protonation: an approach to optically active α-amino thioester derivatives. Org. Biomol. Chem., 2012, 10, 490-494.
71. Hayashi, M.; Nakamura, S. Catalytic enantioselective protonation of α-oxygenated ester enolates prepared through phospha-Brook rearrangement. Angew. Chem. Int. Ed. Engl., 2011, 50, 2249-2252.
72. Oku, M.; Arai, S.; Katayama, K.; Shioiri, T. Catalytic synthesis of allenes via isomerization of alkynes under phase transfer catalyzed conditions. Synlett, 2000, 493-494.
73. Hintermann, L.; Schmitz, M. Enantioselective synthesis of phospholenes via asymmetric organocatalytic alkene isomerization. Adv. Synth. Catal., 2008, 350, 1469-1473
74. Hintermann, L.; Schmitz, M.; Maltsev, O.V.; Naumov, P. Organocatalytic stereo-somerization versus alkene isomerization: catalytic asymmetric synthesis of 1-hydroxy-trans-2,5-diphenylphospholane 1-oxide. Synthesis, 2013, 308-325.
75. Liu, H.; Leow, D.; Huang, K.-W.; Tan, C.-H. Enantioselective synthesis of chiral allenoates by guanidine-catalyzed isomerization of 3-alkynoates. J. Am. Chem. Soc., 2009, 131, 7212-7213
76. Liu, H.; Feng, W.; Kee, C.W.; Leow, D.; Loh, W.-T.; Tan, C.-H. Brønsted base-catalyzed tandem isomerization-Michael reactions of alkynes: synthesis of oxacycles and azacycles. Adv. Synth. Catal., 2010, 352, 3373-3379.
77. Inokuma, T.; Furukawa, M.; Suzuki, Y.; Kimachi, T.; Kobayashi, Y.; Takemoto, Y. Organocatalyzed isomerization of α-substituted alkynoates into trisubstituted allenoates by dynamic kinetic resolution. Chem Cat Chem, 2012, 983-985.
78. Wu, Y.; Singh, R.P.; Deng, L. Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule. J. Am. Chem. Soc., 2011, 133, 12458-12461
79. Xue, X.-S.; Li, X.; Yu, A.; Yang, C.; Song, C.; Cheng, J.-P. Mechanism and selectivity of bioinspired cinchona alkaloid derivatives catalyzed asymmetric olefin isomerization: a computational study. J. Am. Chem. Soc., 2013, 135, 7462-7473.
80. Lee, J.H.; Deng, L. Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst. J. Am. Chem. Soc., 2012, 134, 18209-18212.