Catalytic enantioselective aryl transfer to aldehydes using chiral 2,2'-bispyrrolidine-based salan ligands

Molecules

Volumn 16, Issue 4, 2011, Pages 2971-2981

  Jia, Xuefeng ^a,b   Lin, Aijun ^a   Mao, Zhijie ^a   Zhu, Chengjian ^a,c   Cheng, Yixiang ^d  

^a NANJING UNIVERSITY   (China)

^b SHANXI NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^d NANJING UNIVERSITY   (China)

Author keywords

2,2' bispyrrolidine; Aryl transfer; Arylboronic acid; Enantioselectivity; Salan ligands

Indexed keywords

ALDEHYDE; LIGAND; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIGANDS; PYRROLIDINES; STEREOISOMERISM;

EID: 79955538771     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16042971     Document Type: Article

References (63)

1. Shafi'ee, A.; Hite, G. Absolute configurations of the pheniramines, methyl phenidates, and pipradrols. J. Med. Chem. 1969, 12, 266-270.
2. Ebnother, A.; Weber, H.P. Synthesis and absolute configuration of clemastine and its isomers. Helv. Chim. Acta 1976, 59, 2462-2468.
3. Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, A.; Nagaoka, A. New 1, 4-dihydropyridine derivatives with potent and long-lasting hypotensive effect. Chem. Pharm. Bull. 1985, 33, 3787-3797. (Pubitemid 16235704)
4. Toda, F.; Tanaka, K.; Koshiro, K. A new preparative method for optically active diarylcarbinols. Tetrahedron Asymmetry 1991, 2, 873-874.
5. Casy, A.F.; Drake, A.F.; Ganellin, C.R.; Mercer, A.D.; Upton, C. Stereochemical studies of chiral H-1 antagonists of histamine: The resolution, chiral analysis, and biological evaluation of four antipodal pairs. Chirality 1992, 4, 356-366.
6. Stanev, S.; Rakovska, R.; Berova, N.; Snatzke, G. Synthesis, absolute configuration and circular dichroism of some diarylmethane derivatives. Tetrahedron Asymmetry 1995, 6, 183-198.
7. Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Synthesis of aryl 2- benzofuranyl and 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols. Tetrahedron Asymmetry 1996, 7, 1263-1266. (Pubitemid 26169961)
8. Torrens, A.; Castrillo, J.A.; Claparols, A.; Redondo, J. Enantioselective synthesis of (R)- and (S)- cizolirtine. Application of oxazaborolidine- catalyzed asymmetric borane reduction to azolyl phenyl ketones. Synlett 1999, 765-767. (Pubitemid 29268315)
9. Corey, E.J.; Helal, C.J. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew. Chem. Int. Ed. 1998, 37, 1986-2012. (Pubitemid 28397934)
10. Corey, E.J.; Bakshi, R.K.; Shibata, S. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. J. Am. Chem. Soc. 1987, 109, 5551-5553.
11. Corey, E.J. New enantioselective routes to biologically interesting compounds. Pure Appl. Chem. 1990, 62, 1209-1216.
12. Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Selective hydrogenation of benzophenones to benzhydrols. Asymmetric synthesis of unsymmetrical diarylmethanols. Org. Lett. 2000, 2, 659-662.
13. Noyori, R.; Ohkuma, T. Rapid, productive and stereoselective hydrogenation of ketones. Pure Appl. Chem. 1999, 71, 1493-1501.
14. Pu, L.; Yu, H.-B. Catalytic asymmetric organozinc additions to carbonyl compounds. Chem. Rev. 2001, 101, 757-824. (Pubitemid 35377682)
15. Bolm, C.; Hildebrand, J.P.; Muniz, K.; Hermanns, N. Catalyzed asymmetric arylation reactions. Angew. Chem. Int. Ed. 2001, 40, 3284-3308. (Pubitemid 32916592)
16. Schmidt, F.; Stemmler, R.T.; Rudolph, J.; Bolm, C. Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines. Chem. Soc. Rev. 2006, 35, 454-470. (Pubitemid 44009972)
17. Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Preparation of functionalized dialkylzincs via a boron-zinc exchange. Reactivity and catalytic asymmetric addition to aldehydes. J. Org. Chem. 1996, 61, 8229-8243. (Pubitemid 126552212)
18. Oppolzer, W.; Radinov, R.N.; Sayed, E.E. Catalytic asymmetric synthesis of macrocyclic (E)- allylic alcohols from ω-alkynals via intramolecular 1-alkenylzinc/aldehyde additions. J. Org. Chem. 2001, 66, 4766-4770. (Pubitemid 32861788)
19. Dahmen, S.; Brase, S. [2, 2] Paracyclophane-based N, O-ligands in alkenylzinc additions to Aldehydes. Org. Lett. 2001, 3, 4119-4122. (Pubitemid 33629555)
20. Bolm, C.; Rudolph, J. Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source. J. Am. Chem. Soc. 2002, 124, 14850-14851. (Pubitemid 36014085)
21. Rudolph, J.; Schmidt, F.; Bolm, C. Highly enantioselective synthesis of secondary alcohols using triphenylborane. Adv. Synth. Catal. 2004, 346, 867-872. (Pubitemid 39091015)
22. Braga, A.L.; Luedtke, D.S.; Vargas, F.; Paixao, M.W. Catalytic enantioselective arylation of aldehydes: Boronic acids as a suitable source of transferable aryl groups. Chem. Commun. 2005, 2512-2514. (Pubitemid 40769167)
23. Wu, X.-Y.; Liu, X.-Y.; Zhao, G. Catalyzed asymmetric aryl transfer reactions to aldehydes with boroxines as aryl source. Tetrahedron Asymmetry 2005, 16, 2299-2305. (Pubitemid 40967886)
24. Liu, X.-Y.; Wu, X.-Y.; Chai, Z.; Wu, Y.-Y.; Zhao, G.; Zhu, S.-Z. Highly effective and recyclable dendritic ligands for the enantioselective aryl transfer reactions to aldehydes. J. Org. Chem. 2005, 70, 7432-7435. (Pubitemid 41233288)
25. Bolm, C.; Schmidt, F.; Zani, L. Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes. Tetrahedron Asymmetry 2005, 16, 1367-1376. (Pubitemid 41569230)
26. Dahmen, S.; Lormann, M. Triarylborane ammonia complexes as ideal precursors for arylzinc reagents in asymmetric catalysis. Org. Lett. 2005, 7, 4597-4600. (Pubitemid 41507050)
27. 3. Synlett 2009, 3, 495-499.
28. Ji, J.-X.; Wu, J.; Au-Yeung, T.-T.-L.; Yip, C.W.; Haynes, R.K.; Chan, A.S.C. Highly enantioselective phenyl transfer to aryl aldehydes catalyzed by easily accessible chiral tertiary aminonaphthol. J. Org. Chem. 2005, 70, 1093-1095. (Pubitemid 40189533)
29. Ito, K.; Tomita, Y.; Katsuki, T. Enantioselective phenyl transfer to aldehydes using 1, 1'-bi-2- naphthol-3, 3'-dicarboxamide as chiral auxiliary. Tetrahedron Lett. 2005, 46, 6083-6086. (Pubitemid 41096585)
30. Braga, A.L.; Milani, P.; Vargas, F.; Paixao, M.W.; Sehnem, J.A. Modular chiral thiazolidine catalysts in asymmetric aryl transfer reactions. Tetrahedron Asymmetry 2006, 17, 2793-2797. (Pubitemid 44779269)
31. Wu, P.-Y.; Wu, H.-L.; Uang, B.-J. Asymmetric synthesis of functionalized diarylmethanols catalyzed by a new γ-amino thiol. J. Org. Chem. 2006, 71, 833-835. (Pubitemid 43100785)
32. Lu, G.; Kwong, F.-Y.; Ruan, J.W.; Li, Y.-M.; Chan, A.S.C. Highly enantioselective addition of in situ prepared arylzinc to aldehydes catalyzed by a series of atropisomeric binaphthyl-derived amino alcohols. Chem. Eur. J. 2006, 12, 4115-4120. (Pubitemid 43759735)
33. Jin, M.J.; Sarkar, S.M.; Lee, D.H.; Qiu, H.L. Highly enantioselective aryl transfer to aldehydes: A remarkable effect of sulfur substitution in amino thioacetate ligands. Org. Lett. 2008, 10, 1235-1237.
34. Huang, X.-B.; Wu, L.-L.; Xu, J.-Q.; Zong, L.-L.; Hu, H.-W.; Cheng, Y.-X. Enantioselective arylation of aldehydes catalyzed by a soluble optically active polybinaphthols ligand. Tetrahedron Lett. 2008, 49, 6823-6826.
35. DeBerardinis, A.M.; Turlington, M.; Pu, L. Activation of functional arylzincs prepared from aryl iodides and highly enantioselective addition to aldehydes. Org. Lett. 2008, 10, 2709-2712.
36. Wang, M.-C.; Wang, X.-D.; Ding, X.; Liu, Z.-K. Catalytic asymmetric aryl transfer: Highly enantioselective preparation of (R)- and (S)-diarylmethanols catalyzed by the same chiral ferrocenyl aziridino alcohol. Tetrahedron 2008, 64, 2559-2564.
37. Ruan, J.-W.; Lu, G.; Xu, L.-J.; Li, Y.-M.; Chan, A.S.C. Catalytic asymmetric alkynylation and arylation of aldehydes by an H8-binaphthyl-based amino alcohol ligand. Adv. Synth. Catal. 2008, 350, 76-84.
38. Wang, M.-C.; Zhang, Q.-J.; Zhao, W.-X.; Wang, X.-D.; Ding, X.; Jing, T.-T.; Song, M.-P. N- (Ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol for catalytic asymmetric addition of organozinc reagents to aldehydes. J. Org. Chem. 2008, 73, 168-176.
39. Braga, A.L.; Paixa, M.W.; Westermann, B.; Schneider, P.H.; Wessjohann, L.A. Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. J. Org. Chem. 2008, 73, 2879-2882. (Pubitemid 351485629)
40. Salvi, L.; Kim, J.G.; Walsh, P.J. Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols. J. Am. Chem. Soc. 2009, 131, 12483-12493.
41. Wouters, A.D.; Trossini, G.H.G.; Stefani, H.A.; Lüdtke, D.S. Enantioselective arylations catalyzed by carbohydrate-based chiral amino alcohols. Eur. J. Org. Chem. 2010, 2351-2356.
42. Alexakis, A.; Mangeney, P. Advanced Asymmetric Synthesis; Stephenson, G.R., Ed.; Chapman & Hall: London, UK, 1996; Chapter 5, p. 93.
43. Bennani, Y.L.; Hannessian, S. Trans-1, 2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition. Chem. Rev. 1997, 97, 3161-3195. (Pubitemid 127669618)
44. Lucet, D.; Le Gall, T.; Mioskowski, C. The chemistry of vicinal diamines. Angew. Chem. Int. Ed. 1998, 37, 2580-2627. (Pubitemid 28501504)
45. Hirama, M.; Oishi, T.; Ito, S. Asymmetric dihydroxylation of alkenes with osmium tetroxide: Chiral N, N'-dialkyl-2, 2'-bipyrrolidine complex. Chem. Commun. 1989, 10, 665-666.
46. Oishi, T; Hirama, M. Highly enantioselective dihydroxylation of trans-disubstituted and monosubstituted olefins. J. Org. Chem. 1989, 54, 5834-5835.
47. Oishi, T.; Hirama, M.; Sita, L.R.; Masamune, S. Synthesis of chiral 2, 2'-bipyrrolidine derivatives. Synthesis 1991, 789-792.
48. Kotsuki, H.; Kuzume, H.; Gohda, T.; Fukuhara, M.; Ochi, M.; Oishi, T.; Hirama, M.; Shirot, M. New convenient, enantiospecific synthesis of (S, S)- and (R, R)-2, 2'-bipyrrolidine derivatives. Tetrahedron Asymmetry 1995, 6, 2227-2236.
49. 2 symmetry. Angew. Chem. Int. Ed. 2000, 39, 4093-4095.
50. Denmark, S.E.; Fu, J.-P.; Lawler, M.J. (R, R)-2, 2'- bipyrrolidine and (S, S)-2, 2'-bipyrrolidine: Useful ligands for asymmetric synthesis. Org. Synth. 2006, 83, 121-130.
51. Denmark, S.E.; Fu, J.-P. Catalytic, Enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2, 2'-bispyrrolidine-based bisphosphoramide. J. Am. Chem. Soc. 2001, 123, 9488-9489. (Pubitemid 32900337)
52. Alexakis, A.; Andrey, O. Diamine-catalyzed asymmetric michael additions of aldehydes and ketones to nitrostyrene. Org. Lett. 2002, 4, 3611-3614.
53. Andrey, O.; Alexakis, A.; Bernardinelli, G. Asymmetric michael addition of α-Hydroxyketones to nitroolefins catalyzed by chiral diamine. Org. Lett. 2003, 5, 2559-2561. (Pubitemid 37140907)
54. Andrey, O.; Alexakis, A.; Tomassini, A.; Bernardinelli, G. The use of N-alkyl-2, 2'-bipyrrolidine derivatives as organocatalysts for the asymmetric michael addition of ketones and aldehydes to nitroolefins. Adv. Synth. Catal. 2004, 346, 1147-1168. (Pubitemid 39345676)
55. Mossé, S.; Alexakis, A. First organocatalyzed asymmetric michael addition of aldehydes to vinyl Sulfones. Org. Lett. 2005, 7, 4361-4364. (Pubitemid 41436647)
56. Alexakis, A.; Tomassini, A.; Andrey, O.; Bernardinelli, G. Diastereoselective alkylation of (arene)tricarbonylchromium and ferrocene complexes using a chiral, C2-symmetrical 1, 2-diamine as auxiliary. Eur. J. Org. Chem. 2005, 1332-1339. (Pubitemid 40477402)
57. Denmark, S.E.; Fu, J.-P.; Lawler, M.J. Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides. J. Org. Chem. 2006, 71, 1523-1536.
58. Chen, M.S.; White, M.C. A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science 2007, 318, 783-787. (Pubitemid 351411767)
59. Suzuki, K.; Oldenburg, P.D.; Que, L. Jr. Iron-catalyzed asymmetric olefin cis-dihydroxylation with 97% enantiomeric excess. Angew. Chem. Int. Ed. 2008, 47, 1887-1889.
60. Sergeeva, E.; Kopilov, J.; Goldberg, I.; Kol, M. Salan ligands assembled around chiral bipyrrolidine: Predetermination of chirality around octahedral Ti and Zr centres. Chem. Commun. 2009, 21, 3053-3055.
61. Sergeeva, E.; Kopilov, J.; Goldberg, I.; Kol, M. 2, 2'-Bipyrrolidine versus 1, 2-diaminocyclohexane as chiral cores for helically wrapping diamine-diolate ligands. Inorg. Chem. 2009, 48, 8075-8077.
62. Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. Asymmetric friedel-crafts alkylations of indoles with nitroalkenes catalyzed by Zn(II)-bisoxazoline complexes. J. Org. Chem. 2006, 71, 75-80. (Pubitemid 43128061)
63. Arai, T.; Yokoyama, N. Tandem Catalytic Asymmetric friedel-crafts/henry reaction: Control of three contiguous acyclic stereocenters. Angew. Chem. Int. Ed. 2008, 47, 4989-4992.