Stereoselective heterocycle synthesis through oxidative carbon-hydrogen bond activation

Current Opinion in Drug Discovery and Development

Volumn 13, Issue 6, 2010, Pages 733-747

  Liu, Lei ^a   Floreancig, Paul E ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Biologically active molecule; C H bond activation; heterocycle synthesis; insertion reaction; oxidation reaction; regiocontrol; stereocontrol; synthetic efficiency

Indexed keywords

BENZOQUINONE; CARBON; HYDROGEN; IMIDAZOLE; LITHOSPERMIC ACID; PALLADIUM; STRESS ACTIVATED PROTEIN KINASE INHIBITOR;

CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; REVIEW; STEREOCHEMISTRY;

CARBON; CHEMISTRY, PHARMACEUTICAL; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; OXIDATION-REDUCTION; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM;

EID: 78650166772     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (74)

1. Top 200 pharmaceutical products by worldwide sales in 2009. Mack DJ, Brichacek M, Plichta A, Njardarson JT (2010). cbc.arizona.edu/njardarson/group
2. Lovering F, Bikker J, Humblet C: Escape from fatland: Increasing saturation as an approach to improving clinical success. J Med Chem (2009) 52(21):6752-6756.
3. Godula K, Sames D: C-H bond functionalization in complex organic synthesis. Science (2006) 312(5770):67-72.
4. Davies HM, Beckwith RE: Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion. Chem Rev (2003) 103(8):2861-2903.
5. Giri R, Shi B-F, Engle KM, Maguel N, Yu J-Q: Transition metal-catalyzed C-H activation reactions: Diastereoselectivity and enantioselectivity. Chem Soc Rev (2009) 38(11):3242-3272.
6. Davies HM: Recent advances in catalytic enantioselective C-H functionalization. Angew Chem Int Ed (2006) 45(39): 6422-6425.
7. Wender PA, Verma VA, Paxton TJ, Pillow TH: Function-oriented synthesis, step economy, and drug design. Acc Chem Res (2008) 41(1):40-49.
8. Trost BM: On inventing reactions for atom economy. Acc Chem Res (2002) 35(9):695-705.
9. Blanksby SJ, Ellison GB: Bond dissociation energies of organic molecules. Acc Chem Res (2003) 36(4):255-263.
10. Horita K, Yoshioka T, Tanaka T, Oikawa Y, Yonemitsu O: On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions. Tetrahedron (1986) 42(11):3021-3028.
11. Jung HH, Floreancig PE: Mechanistic analysis of oxidative C-H cleavages using inter- and intramolecular kinetic isotope effects. Tetrahedron (2009) 65(52):10830-10836.
12. Hayashi Y, Mukaiyama T: New method for oxidative carbon-carbon bond formation by the reaction of allyl ethers, 2,3-dichloro-5,6-dicyano-p- benzoquinone (DDQ) and silyl carbon nucleophiles. Chem Lett (1987) 16(9):1811-1814.
13. Xu YC, Lebeau E, Gillard JW, Attardo G: Regio- and stereoselective, DDQ-induced oxidative coupling of isochromans and isothiochroman with alcohols. Tetrahedron Lett (1993) 34(24):3841-3844.
14. Xu YC, Roy C, Lebeau E: DDQ-induced and stereoselective functionalization at heterosubstituted benzylic positions by carbon nucleophiles. Tetrahedron Lett (1993) 34(51):8189-8192.
15. Xu YC, Kohlman DT, Liang SX, Erikkson C: Stereoslective, oxidative C-C bond coupling of naphthopyran induced by DDQ: Stereocontrolled total synthesis of deoxyfrenolicin. Org Lett (1999) 1(10):1599-1602.
16. Dubs C, Hamashima Y, Samamoto N, Seidel TM, Suzuki S, Hashizume D, Sodeoka M: Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines. J Org Chem (2008) 73(15):5859-5871.
17. Li CJ: Cross-dehydrogenative coupling (CDC): Exploring C-C bond formations beyond functional group transformations. Acc Chem Res (2009) 42(2):335-344.
18. 3 C-H bonds adjacent to a nitrogen atom. Org Lett (2004) 6(26):4997-4999. (Pubitemid 40125861)
19. Du X, Houk KN: Transition states for alkane oxidations by dioxiranes. J Org Chem (1998) 63(19):6480-6483.
20. Glukhovtsev MN, Canepa C, Bach RD: The nature of the transition structure for the oxidation of alkanes with dioxiranes. J Am Chem Soc (1998) 120(40):10528-10533.
21. Wender PA, Hilinski MK, Mayweg AVW: Late-stage intermolecular CH activation for lead diversifcation: A highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues. Org Lett (2005) 7(1): 79-82.
22. 3 C-H bond arylation directed by amidine protecting group: α-Arylation of pyrrolidines and piperidines. J Am Chem Soc (2006) 128(44):14220-14221.
23. Robertson J, Pillai J, Lush RK: Radical translocation reactions in synthesis. Chem Soc Rev (2001) 30(2):94-103.
24. Martín A, Pérez-Martín I, Suárez E: Intramolecular hydrogen abstraction promoted by amidyl radicals. Evidence for electronic factors in the nucleophilic cyclization of ambident amides to oxocarbenium ions. Org Lett (2005) 7(10):2027-2030.
25. Francisco CG, Freire R, Herrera AJ, Pérez-Martín I, Suárez E: Intramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrate models. Org Lett (2002) 4(11):1959-1961.
26. Meth-Cohn O: The t-amino effect: Heterocycles formed by ring closure of ortho-substituted t-anilines. Adv Heterocycl Chem (1996) 65:1-37.
27. Nijhuis WHN, Verboom W, El-Fadl AA, Harkema S, Reinhoudt DN: Stereochemical aspects of the "tert-amino effect". 1. Regioselectivity in the synthesis of pyrrolo[1,2-a]quinolines and benzo[c]quinolizines. J Org Chem (1989) 54(1):199-209.
28. Murarka S, Deb I, Zhang C, Seidel D: Catalytic enantioselective intramolecular redox reactions: Ring-fused tetrahydro-quinolines. J Am Chem Soc (2009) 131(37):13226-13227.
29. 3 C-H functionalization via a Lewis acid-catalyzed intramolecular redox event. J Am Chem Soc (2005) 127(35):12180-12181.
30. Gassman PG, Singleton DA, Wilwerding JJ, Chavan SP: Acrolein acetals as allyl cation precursors in the ionic Diels-Alder reaction. J Am Chem Soc (1987) 109(7):2182-2184.
31. 3 C-H bonds and reactive alkenyl oxocarbenium intermediates. J Am Chem Soc (2009) 131(2):402-403.
32. 3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/ cyclization. Org Lett (2005) 7(24):5429-5431.
33. McQuaid KM, Long JZ, Sames D: C-H bond functionalization via hydride transfer: Synthesis of dihydrobenzopyrans from ortho-vinylaryl alkyl ethers. Org Lett (2009) 11(14): 2972-2975.
34. Shikanai D, Murase H, Hata T, Urabe H: Rh-catalyzed isomerization and intramolecular redox reaction of alkynyl ethers affording dihydropyrans and ketoolefns. J Am Chem Soc (2009) 131(9):3166-3167.
35. Jurberg ID, Odabachian Y, Gagosz F: Hydroalkylation of alkynyl ethers via a gold(Ι)-catalyzed 1,5-hydride shift/cyclization sequence. J Am Chem Soc (2010) 132(10):3543-3552.
36. 3 C-H bonds catalyzed by platinum tetraiodide. J Am Chem Soc (2009) 131(45):16525-16528.
37. Tu W, Liu L, Floreancig PE: Diastereoselective tetrahydropyrone synthesis through transition-metal-free oxidative carbon-hydrogen bond activation. Angew Chem Int Ed (2008) 47(22):4184-4187.
38. Yu B, Jiang T, Li J, Su Y, Pan X, She X: A novel Prins cyclization through benzylic/allylic C-H activation. Org Lett (2009) 11(15):3442-3445.
39. Tu W, Floreancig PE: Oxidative carbocation formation in macrocycles: Synthesis of the neopeltolide macrocycle. Angew Chem Int Ed (2009) 48(25):4567-4571.
40. Cui Y, Tu W, Floreancig PE: Total synthesis of neopeltolide and analogs. Tetrahedron (2010) 66(26):4867-4873.
41. Liu L, Floreancig PE: Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions. Angew Chem Int Ed (2010) 49(34):5894-5897.
42. Liu L, Floreancig PE: Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation. Angew Chem Int Ed (2010) 49(17):3069-3072.
43. Rice GT, White MC: Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs. J Am Chem Soc (2009) 131(33):11707-11711.
44. Qi X, Rice GT, Lall MS, Plummer MS, White MC: Diversifcation of a β-lactam pharmacophore via allylic C-H amination: Acceralating effect of Lewis acid co-catalyst. Tetrahedron (2010) 66(26):4816-4826.
45. Fraunhoffer KF, Prabagaran N, Sirois LE, White MC: Macro- lactonization via hydrocarbon oxidation. J Am Chem Soc (2006) 128(28):9032-9033.
46. Stang EM, White MC: Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidation. Nat Chem (2009) 1(7):547-551.
47. McDonald RI, Stahl SS: Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides. Angew Chem Int Ed (2010) 49(32):5529-5532.
48. Davies HML, Manning JR: Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion. Nature (2008) 451(7177):417-424.
49. Doyle MP, Duffy R, Ratnikov M, Zhou L: Catalytic carbene insertion into C-H bonds. Chem Rev (2010) 110(2):704-724.
50. Breslow R, Gellman SH: Intramolecular nitrene C-H insertions mediated by transition-metal complexes as nitrogen analogues of cytochrome P-450 reactions. J Am Chem Soc (1983) 105(22):6728-6729.
51. Espino CG, Wehn PM, Chow J, Du Bois J: Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation. J Am Chem Soc (2001) 123(28):6935-6936.
52. Wehn PM, Lee J, Du Bois J: Stereochemical models for Rh-catalyzed amination reactions of chiral sulfamates. Org Lett (2003) 5(25):4823-4826.
53. Wehn PM, Du Bois J: Enantioselective synthesis of the bromopyrrole alkaloids manzacidin A and C by stereospecifc C-H bond oxidation. J Am Chem Soc (2002) 124(44): 12950-12951.
54. Espino CG, Du Bois J: A Rh-catalyzed C-H insertion reaction for the oxidative conversion of carbamates to oxazolidinones. Angew Chem Int Ed (2001) 40(3):598-600. (Pubitemid 32146180)
55. Hinman A, Du Bois J: A stereoselective synthesis of (-)-tetrodotoxin. J Am Chem Soc (2003) 125(38):11510-11511.
56. Kim M, Mulcahy JV, Espino CG, Du Bois J: Expanding the substrates scope for C-H amination reactions: Oxidative cyclization of urea and guanidine derivatives. Org Lett (2006) 8(6):1073-1076.
57. Zalatan DN, Du Bois J: A chiral rhodium carboxaidate catalyst for enantioselective C-H amination. J Am Chem Soc (2008) 130(29):9220-9221.
58. Liang JL, Yuan SX, Huang JS, Yu WY, Che CM: Highly diastereo-and enantioselective intramolecular amidation of saturated C-H bonds catalyzed by ruthenium porphyrins. Angew Chem Int Ed (2002) 41(18):3465-3468.
59. Milczek E, Boudet N, Blakey S; Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts. Angew Chem Int Ed (2008) 47(36):6825-6828.
60. Cui Y, He C: A silver-catalyzed intramolecular amidation of saturated C-H bonds. Angew Chem Int Ed (2004) 43(32): 4210-4212.
61. Lebel H, Huard K, Lectard S: N-tosyloxycarbamates as a source of metal nitrenes: Rhodium-catalyzed C-H insertion and aziridination reactions. J Am Chem Soc (2005) 127(41): 14198-14199.
62. Chen MS, White MC: A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science (2007) 318(5851):783-787.
63. Vermeulen NA, Chen MS, White MC: The Fe(PDP)-catalyzed aliphatic C-H oxidation: A slow addition protocol. Tetrahedron (2009) 65(16):3078-3084.
64. Harada H, Thalji RK, Bergman RG, Ellman JA: Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation. J Org Chem (2008) 73(17):6772-6779.
65. O'Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA: Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation. J Am Chem Soc (2005) 127(39):13496-13497.
66. Rech JC, Yato M, Duckett D, Ember B, LoGrasso PV, Bergman RG, Ellman JA: Synthesis of potent bicyclic bisarylimidazole c-jun N-terminal kinase inhibitors by catalytic C-H bond activation. J Am Chem Soc (2007) 129(3):490-491.
67. Tsai AS, Wilson RM, Harada H, Bergman RG, Ellman JA: Rhodium catalyzed enantioselective cyclization of substituted imidazoles via C-H bond activation. Chem Commun (2009) (26):3910-3912.
68. Ferreira EM, Stoltz BM: Catalytic C-H bond functionalization with palladium(II): Aerobic oxidative annulations of indoles. J Am Chem Soc (2003) 125(32):9578-9579.
69. Ferreira EM, Zhang H, Stoltz BM: C-H Bond functionalization with palladium(II): Intramolecular oxidative annulations of arenes. Tetrahedron (2008) 64(26):5987-6001.
70. Yoshida J-i, Suga S: Basic concepts of "cation pool" and "cation fow" methods and their applications in conventional and combinatorial organic synthesis. Chem Eur J 2002 8(12): 2650-2658.
71. Yun SY, Zheng J-C, Lee D: Stereoelectronic effect for the selectivity in C-H insertion of alkylidene carbenes and its application to the synthesis of platensimycin. J Am Chem Soc (2009) 131(24):8413-8415.
72. Chen K, Eschenmoser A, Baran PS: Strain release in C-H bond activation Angew Chem Int Ed (2009) 48(51):9705-9708.
73. Chen MS, White MC: Combined effects on selectivity in Fe-catalyzed methylene oxidation. Science (2010) 327(5965): 566-571.
74. 3)-H bonds using monoprotected amino acids as chiral ligands. Angew Chem Int Ed (2008) 47(26):4882-4886.