Organocatalytic application of axially dissymmetric BINOLs and their conversion into binaphthyl phosphoric acids

Current Organic Chemistry

Volumn 16, Issue 15, 2012, Pages 1730-1753

  Bhadury, Pinaki S ^a   Yao, Yuanyong ^a   He, Yongguang ^a  

^a GUIZHOU UNIVERSITY   (China)

Author keywords

Asymmetric Organocatalysis; Chiral Phosphoric Acids; Dissymmetric BINOL; Hydrogen Bond; Synthesis

Indexed keywords

CATALYSTS; HYDROGEN BONDS;

ASYMMETRIC ORGANOCATALYSIS; BINAPHTHYL; BRONSTED ACIDS; CHIRAL PHOSPHORIC ACID; DISSYMMETRIC BINOL; ORGANIC TRANSFORMATIONS; ORGANOCATALYSTS; ORGANOCATALYTIC; STEREOSELECTIVE TRANSFORMATIONS; STERICALLY DEMANDING;

PHOSPHORIC ACID;

EID: 84864551135     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212802651313     Document Type: Review

References (64)

1. Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Chiral Brønsted acid catalyzedenantioselective hydrophosphonylation of imines: asymmetric synthesis of α-amino phosphonates. Org. Lett., 2005, 7, 2583-2585.
2. Xu, W.M.; Zhang, S.; Yang, S.; Jin, L.H.; Bhadury, P.S.; Hu, D.Y.; Zhang, Y. Asymmetric synthesis of α-aminophosphonates using the inexpensivechiral catalyst 1,1'-binaphthol phosphate. Molecules, 2010, 15, 5782-5796.
3. Simón, L.; Goodman, J.M. A model for the enantioselectivity of imine reactionscatalyzed by BINOL-phosphoric acid catalysts. J. Org. Chem., 2011,76, 1775-1788.
4. Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. Chiral Brønsted acidcatalyzed enantioselective Mannich-type reaction. J. Am. Chem. Soc., 2007,129, 6756-6764.
5. Guo, Q.X.; Liu, H.; Guo, C.; Luo, S.W.; Gu, Y.; Gong, L.Z. Chiral Brønstedacid-catalyzed direct asymmetric Mannich reaction. J. Am. Chem. Soc., 2007,129, 3790-3791.
6. Ii, G.L.; Liang, Y.X.; Antilla, J.C. A vaulted biaryl phosphoric acidcatalyzedreduction of α-imino esters: the highly enantioselective preparationof α-amino esters. J. Am. Chem. Soc., 2007, 129, 5830-5831.
7. Bhadury, P.S.; Li, H. Organocatalytic asymmetric hydrophosphonylation/Mannich reactions using thiourea, cinchona and Brnsted acid catalysts. Synlett., 2012, 23, 1108-1131.
8. Seayad, J.; Seayad, A.M.; List, B. Catalytic asymmetric Pictet-Spenglerreaction. J. Am. Chem. Soc., 2006, 128, l086-1087.
9. Rowland, G.B.; Zhang, H.; Rowland, E.B.; Chennamadhavuni, S.; Wang, Y.;Antilla, J.C. Brønsted acid-catalyzed imine amidation. J. Am. Chem. Soc.,2005, 127, 15696-15697.
10. Chen, X.H.; Xu, X.Y.; Liu, H.; Cun, L.F.; Gong, L.Z. Highly enantioselectiveorganocatalytic Biginelli reaction. J. Am. Chem. Soc., 2006, 128, 14802-14803.
11. Rowland, G.B.; Rowland, E.B.; Liang, Y.X.; Perman, J.A.; Antilla, J.C. Thehighly enantioselective addition of indoles to N-acyl imines with use of achiral phosphoric acid catalyst. Org. Lett., 2007, 9, 2609-2611.
12. Fleischmann, M.; Drettwan, D.; Sugiono, E.; Rueping, M.; Gschwind, R.M. Brønsted acid catalysis: hydrogen bonding versus ion pairing in imine activation. Angew. Chem. Int. Ed., 2011, 50, 6364-6369.
13. Lundy, B. J; Jansone-Popova, S; May, J.A. Enantioselective conjugate additionof alkenylboronic acids to indole-appended enones. Org. Lett., 2011, 13,4958-4961.
14. Belokon, Y.N.; Gugkaeva, Z.T.; Maleev, V.I.; Moskalenko, M.A.; Tsaloev, A.T.; Khrustalev, V.N.; Hakobyan, K.V. Four hydroxyls are better than two. The use of a chiral lithium salt of 3,3'-bis-methanol-2,2'-binaphthol as amultifunctional catalyst of enantioselective Michael addition reactions. Tetrahedron:Asymmetry, 2011, 22, 167-172.
15. Hatano, M.; Horibe, T.; Ishihara, K. Chiral lithium(I) binaphtholate salts forthe enantioselective direct Mannich-type reaction with a change of syn/antiand absolute stereochemistry. J. Am. Chem. Soc., 2010, 132, 56-57.
16. Ichibakase, T.; Nakatsu, M.; Nakajima, M. Enantioselective Evans-Tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate. Molecules, 2011, 16, 5008-5019.
17. Li, H.; Da, C.S.; Xiao, Y.H.; Li, X.; Su, Y.N. Direct asymmetric Aldolreaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOLderivedzincate catalyst. J. Org. Chem., 2008, 73, 7398-7403.
18. Roush, W.R. In: Comprehensive Organic Synthesis; Trost, B. A.; Fleming, I., Ed.; Permagon Press: U.K., 1991, Vol. 2.
19. Chemler, S.R.; Roush, W. R. In: Modern Carbonyl Chemistry; Otera, J., Ed.;Wiley-VCH: Germany, 2000; Chapter 11, pp. 403.
20. Denmark, S. E.; Almstead, N. G. In: Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Germany, 2000; Chapter 10, pp. 299.
21. Lou, S.; Moquist, P.N.; Schaus, S.E. Asymmetric allylboration of ketonescatalyzed by chiral diols. J. Am. Chem. Soc., 2006, 128, 12660-12661.
22. Lou, S.; Moquist, P.N.; Schaus, S.E. Asymmetric allylboration of acyl iminescatalyzed by chiral diols. J. Am. Chem. Soc., 2007, 129, 15398-15404.
23. Pellegrinet, S.C.; Goodman, J.M. Asymmetric conjugate addition of alkynylboronatesto enones: rationale for the intriguing catalysis exerted by binaphthols.J. Am. Chem. Soc., 2006, 128, 3116-3117.
24. Paton, R.S.; Goodman, J.M.; Pellegrinet, S.C. Theoretical study of theasymmetric conjugate alkenylation of enones catalyzed by binaphthols. J. Org. Chem., 2008, 73, 5078-5089.
25. Yamomoto, H.; Futatsugi, K. Designer acids: combined acid catalysis forasymmetric synthesis. Angew. Chem. Int. Ed., 2005, 44, 1924-1942.
26. Turner, H.M.; Patel, J.; Niljianskul, N.; Chong, J.M. Binaphthol-catalyzedasymmetric conjugate arylboration of enones. Org. Lett., 2011, 13, 5796-5799.
27. Ichibakase, T.; Nakajima, M. Direct enantioselective Aldol-Tishchenkoreaction catalyzed by chiral lithium diphenylbinaphtholate. Org. Lett., 2011,13, 1579-1581.
28. Momiyama, N.; Yamamoto, Y.; Yamamoto, H. Diastereo-and enantioselectivesynthesis of nitroso Diels-Alder-type bicycloketones using dienamine:mechanistic insight into sequential nitroso aldol/Michael reaction and applicationfor optically pure 1-amino-3, 4-diol synthesis. J. Am. Chem. Soc.,2007, 129, 1190-1195.
29. Barnett, D.S.; Schaus, S.E. Asymmetric propargylation of ketones usingallenylboronates catalyzed by chiral biphenols. Org. Lett., 2011, 13, 4020-4023.
30. Kodama, H.; Junji Ito, A.N.; Ohta, T.; Furukawa, I. Enantioselective additionof diethylzinc to aldehydes catalyzed by 3,3'-bis(2-oxazolyl)-1,1'-bi-2-naphthol (BINOL-Box) ligands derived from 1,1'-bi-2-naphthol. Appl. Organometal. Chem., 2000, 14, 709-714.
31. 2Zn to aldehydes. Org. Lett., 2007, 9, 4403-4406.
32. Xu, M.H.; Pu, L. A new 1,1'-binaphthyl-based catalyst for the enantioselectivephenylacetylene addition to aromatic aldehydes without using a titaniumcomplex. Org. Lett., 2002, 4, 4555-4557.
33. Turlington, M.; Pu, L. Asymmetric alkyne addition to aldehydes catalyzed byBINOL and Its derivatives. Synlett, 2012, 23, 649-684.
34. Matsui, K.; Takizawa, S.; Sasai, H. Bifunctional organocatalysts for enantioselectiveaza-Morita-Baylis-Hillman reaction. J. Am. Chem. Soc., 2005,127, 3680-3681.
35. Takizawa, S.; Horii, A.; Sasai, H. Acid-base organocatalysts for the aza-Morita-Baylis-Hillman reaction of nitroalkenes. Tetrahedron: Asymmetry,2010, 21, 891-894.
36. Wang, Q.; Chen, X.; Tao, L.; Wang, L.; Xiao, D.; Yu, X.Q.; Pu, L. Enantioselectivefluorescent recognition of amino alcohols by a chiral tetrahydroxyl1,1'-binaphthyl compound. J. Org. Chem., 2007, 72, 97-101.
37. Lu, Q. S; Dong, L.; Zhang, J.; Li, J.; Jiang, L.; Huang, Y.; Qin, S.; Hu, C.W.;Yu, X.Q. Imidazolium-functionalized binol as a multifunctional receptor forchromogenic and chiral anion recognition. Org. Lett., 2009, 11, 669-672.
38. Xu, K.X.; Qiu, Z.; Zhao, J.J.; Zhao, J.; Wang C.J. Enantioselective fluorescentsensors for amino acid derivatives based on binol bearing benzoyl unit. Tetrahedron: Asymmetry, 2009, 20, 1690-1696.
39. Heo, J.; Mirkin, C.A.; Allosteric, P. Recognition of mandelic acid with anenantioselective coordination complex. Angew. Chem. Int. Ed., 2006, 45, 941-944.
40. Liu, H.L.; Zhu, H.P.; Hou, X. L.; Pu, L. Highly enantioselective fluorescentrecognition of serine and other amino acid derivatives. Org. Lett., 2010, 12,4172-4175.
41. Pu, L. Enantioselective fluorescent sensors: a tale of BINOL. Acc. Chem. Res., 2012, 45, 150-163.
42. Xu, K.X.; Cheng, P.F.; Zhao, J.; Wang, C.J. Enantioselective fluorescentsensors for amino acid derivatives based on binol bearing s-tryptophan unit:synthesis and chiral recognition. J. Fluoresc., 2011, 21, 991-1000.
43. Bunzen, J.; Kiehne, U.; Christian B.S.; Lützen, A. Immobilization ofbis(bipyridine) binol ligands and their use in chiral resolution. Org. Lett.,2009, 11, 4786-2789.
44. Doria, F.; Richter, S.N.; Nadai, M.; Stefano C.M.; Mella, M.; Palumbo, M.;Freccero, M. BINOL-amino acid conjugates as triggerable carriers of DNAtargetedpotent photocytotoxic agents. J. Med. Chem., 2007, 50, 6570-6579.
45. Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. A new bifunctionalasymmetric catalysis: an efficient catalytic asymmetric cyanosilylation of aldehydes.J. Am. Chem. Soc., 1999, 121, 2641-2642.
46. Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. Lanthanide-catalyzedasymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using 3,3'-bis(2-oxazolyl)-1,1'-bi-2-naphthol (binol-box) ligands. J. Organomet. Chem.,2000, 603, 6-12.
47. Casas, J.; Náera, C.; Sansano, J.M.; Saá, J.M. Binolam, a recoverable chiralligand for bifunctional enantioselective catalysis: the asymmetric synthesisof cyanohydrins. Org. Lett., 2002, 4, 2589-2592.
48. Qin, Y.C.; Liu, L.; Pu, L. One-step synthesis of a bifunctional binol ligandfor the highly enantioselective cyanation of aliphatic aldehydes. Org. Lett.,2005, 12, 2381-2383.
49. Stefano C.M.; Doria, F.; Verga, D.; Freccero, M. Photogenerated quinonemethides as useful intermediates in the synthesis of chiral binol ligands. J. Org. Chem., 2006, 71, 3889-3895.
50. Coluccini, C.; Castelluccio, A.; Pasini, D. Chemoselective functionalizationof 3, 3'-substituted binol derivatives. J. Org. Chem., 2008, 73, 4237-4240.
51. Yang, X.B.; Feng, J.; Zhang, J.; Wang, N.; Wang, L.; Liu, J.L.; Yul, X.Q. Highly enantioselective hetero-Diels-Alder reaction of trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydescatalyzed by 3-substituted binol-titanium complex. Org. Lett., 2008,10, 1299-1302.
52. Endo, K.; Tanaka, K.; Ogawa, M.; Shibata, T. Multinuclear Pd/Zn complexcatalyzedasymmetric alkylative ring-opening reaction of oxabicyclic alkenes. Org. Lett., 2011, 13, 868-871.
53. Hou, Z.R.; Wang, J.; He, P.; Wang, J.; Qin, B.; Liu, X.H.; Lin, L.L.; Feng, X.M. Highly enantioselective insertion of carbenoids into N-H bonds catalyzedby copper(I) complexes of binol derivatives. Angew. Chem., 2010, 122,4873-4876.
54. Zhang, Z.G.; Dong, Z.B.; Li, J.S. Synthesis and application of 3-substituted(S)-binol as shiral ligands for the asymmetric ethylation of aldehydes. Chirality, 2010, 22, 820-826.
55. Bai, S.; Liang, X.P.; Song, B.A.; Bhadury, P.S.; Hu, D.Y.; Yang, S. AsymmetricMannich reactions catalyzed by cinchona alkaloid thiourea: enantioselectiveone-pot synthesis of novel β-amino ester derivatives. Tetrahedron:Asymmetry, 2011, 22, 518-523.
56. Li, L.; Song, B.A.; Bhadury, P.S.; Zhang, Y.P.; Hu, D.Y.; Yang, S. Enantioselectivesynthesis of ss-amino esters bearing a benzothiazole moiety via aMannich-type reaction catalyzed by a cinchona alkaloid. Eur. J. Org. Chem.,2011, 4743-4746.
57. Bai, S.; Song, B.A.; Bhadury, P.S.; Yang, S.; Hu, D.Y.; Xue, W. [BMIM]ClCatalyzed one-pot synthesis of α-aminophosphonate derivatives containing a4-phenoxyquinazoline moiety under microwave irradiation. Chin. J. Chem.,2011, 29, 109-117.
58. Li, W.H.; Song, B.A.; Bhadury, P.S.; Li, L.; Wang, Z.C.; Zhang, X.Y.; Hu, D.Y.; Chen, Z.; Zhang, Y.P.; Bai, S.; Wu, J.; Yang, S. Chiral cinchona alkaloid-derived thiourea catalyst for enantioselective synthesis of novel β-aminoesters by Mannich reaction. Chirality, 2012, 24, 223-231.
59. Bhadury, P.S.; Song, B.A.; Yang, S.; Zhang, Y.P.; Zhang, S. Some potentialchiral catalysts for preparation of asymmetric α-aminophosphonates. Curr. Org. Synth., 2008, 5, 134-150.
60. Bhadury, P.S.; Song, B.A.; Yang, S.; Hu, D. Y; Xue, W. Bifunctional chiralorganocatalysts in organic transformations. Curr. Org. Synth., 2009, 6, 380-399.
61. Bhadury, P.S.; Zhang, Y.P.; Zhang, S.; Song, B.A.; Yang, S.; Hu, D.Y.;Chen, Z.; Xue, W.; Jin, L.H. An effective route to fluorine containing asymmetricα-aminophosphonates using chiral Bronsted acid catalyst. Chirality,2009, 21, 547-557.
62. Song, B.A.; Yang, S.; Jin, L.H.; Bhadury, P.S. Environment-Friendly AntiviralAgents for Plants; Eds.; Springer: Jointly published with Chemical IndustryPress, 2010.
63. Bhadury, P.S.; Song, B.A. Chemistry of organocatalytic asymmetric Mannichreactions. Curr. Org. Chem., 2010, 14, 1989-2006.
64. Bhadury, P.S.; Yang, S.; Song, B.A. Catalytic synthesis of optically active β-amino acid derivatives. Curr. Org. Synth., 2012, 9, doi:10.2174/1570212700121031794.