Circular dichroism sensing of chiral compounds using an achiral metal complex as probe

Chirality

Volumn 26, Issue 8, 2014, Pages 379-384

  Irfanoglu, Burcin ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

chiral amplification; chiroptical sensor; Cobalt(salen) complex; enantioselective analysis

Indexed keywords

COBALT COMPLEX; METAL COMPLEX;

ARTICLE; CHELATION; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; ENANTIOSELECTIVITY; HIGH THROUGHPUT SCREENING; OXIDATION; PRIORITY JOURNAL;

EID: 84904817833     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22332     Document Type: Article

References (54)

1. Berova N, Di Bari L, Pescitelli G,. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 2007; 36: 914-931.
2. Leung D, Kang SO, Anslyn EV,. Rapid determination of enantiomeric excess: a focus on optical approaches. Chem Soc Rev 2012; 41: 448-479.
3. For an example of chirality CPL sensing:, Song F, Wei G, Jiang X, Li F, Cheng Y, Zhu C,. Chiral sensing for induced circularly polarized luminescence using an Eu(III)-containing polymer and D- or L-proline. Chem Commun 2013; 49: 5772-5774.
4. Katoono R, Kawai H, Fujiwara K, Suzuki T,. Change in conformation upon complexation of double-armed terephthalamide hosts: dynamic molecular recognition of ditopic guests with strong CD signaling. Tetrahedron Lett 2006; 47: 1513-1518. (Pubitemid 43187945)
5. For a review of supramolecular sensors:, Hembury GA, Borovkov VV, Inoue Y,. Chirality-sensing supramolecular systems. Chem Rev 2008; 108: 1-73. (Pubitemid 351176405)
6. Superchi S, Casarini D, Laurita A, Bavoso A, Rosini C,. Induction of a preferred twist in a biphenyl core by stereogenic centers: a novel approach to the absolute configuration of 1,2- and 1,3-diols. Angew Chem Int Ed 2001; 40: 451-454. (Pubitemid 32114902)
7. n/Val oligopeptides. J Am Chem Soc 2004; 126: 12874-12879. (Pubitemid 39372317)
8. Superchi S, Bisaccia R, Casarini D, Laurita A, Rosini C,. Flexible biphenyl chromophore as a circular dichroism probe for assignment of the absolute configuration of carboxylic acids. J Am Chem Soc 2006; 128: 6893-6902. (Pubitemid 43830576)
9. Dutot L, Wright K, Gaucher Wakselman M, Mazaleyrat JP, De Zotti M, Peggion C, Formaggio F, Toniolo C,. The Bip method, based on the induced circular dichroism of a flexible biphenyl probe in terminally protected -Bip-Xaa - dipeptides, for assignment of the absolute configuration of β-amino acids. J Am Chem Soc 2008; 130: 5986-5992. (Pubitemid 351620845)
10. Kuwahara S, Nakamura M, Yamaguchi A, Ikeda M, Habata Y,. Combination of a new chiroptical probe and theoretical calculations for chirality detection of primary amines. Org Lett 2013; 15: 5738-5741.
11. Sciebura J, Skowronek P, Gawronski J,. Trityl ethers: molecular bevel gears reporting chirality through circular dichroism spectra. Angew Chem Int Ed 2009; 48: 7069-7072.
12. Sciebura J, Gawronski J,. Double chirality transmission in trityl amines: Sensing molecular dynamic stereochemistry by circular dichroism and DFT calculations. Chem Eur J 2011; 17: 13138-13141.
13. Katoono R, Kawai H, Fujiwara K, Suzuki T,. Dynamic molecular propeller: supramolecular chirality sensing by enhanced chiroptical response through the transmission of point chirality to mobile helicity. J Am Chem Soc 2009; 131: 16896-16904.
14. Tartaglia S, Pace F, Scafato P, Rosini C,. A new case of induced helical chirality in a bichromophoric system: absolute configuration of transparent and flexible diols from the analysis of the electronic circular dichroism spectra of the corresponding di(1-naphthyl)ketals. Org Lett 2008; 10: 3421-3424.
15. Kim H, So SM, Yen CPH, Vinhato E, Lough AJ, Hong JI, Kim HJ, Chin J,. Highly stereospecific generation of helical chirality by imprinting with amino acids: a universal sensor for amino acid enantiopurity. Angew Chem Int Ed 2008; 47: 8657-8660.
16. Proni G, Pescitelli G, Huang X, Nakanishi K, Berova N,. Magnesium tetraarylporphyrin tweezer: a CD-sensitive host for absolute configurational assignments of α-chiral carboxylic acids. J Am Chem Soc 2003; 125: 12914-12927. (Pubitemid 37280460)
17. Huang X, Fujioka N, Pescitelli G, Koehn FE, Williamson RT, Nakanishi K, Berova N,. Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host. J Am Chem Soc 2002; 124: 10320-10335. (Pubitemid 34977387)
18. Balaz M, De Napoli M, Holmes AE, Mammana A, Nakanishi K, Berova N, Purrello R,. A cationic zinc porphyrin as a chiroptical probe for Z-DNA. Angew Chem Int Ed 2005; 44: 4006-4009. (Pubitemid 40886432)
19. Berova N, Pescitelli G, Petrovic AG, Proni G,. Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts. Chem Commun 2009: 5958-5980.
20. Joyce LA, Maynor MS, Dragna JM, Da Cruz GM, Lynch VM, Canary JW, Anslyn EV,. A simple method for the determination of enantiomeric excess and identity of chiral carboxylic acids. J Am Chem Soc 2011; 133: 13746-13752.
21. You L, Pescitelli G, Anslyn EV, Di Bari L,. An exciton-coupled circular dichroism protocol for the determination of identity, chirality, and enantiomeric excess of chiral secondary alcohols. J Am Chem Soc 2012; 134: 7117-7125.
22. You L, Berman JS, Lucksanawichien A, Anslyn EV,. Correlating sterics parameters and diastereomeric ratio values for a multicomponent assembly to predict exciton-coupled circular dichroism intensity and thereby enantiomeric excess of chiral secondary alcohols. J Am Chem Soc 2012; 134: 7126-7134.
23. Joyce L, Canary J, Anslyn EV,. Enantio- and chemoselective differentiation of protected α-amino acids and β-homoamino acids with a single copper(II) host. Chem Eur J 2012; 18: 8064-8069.
24. Zhang J, Holmes AE, Sharma A, Brooks NR, Rarig RS, Zubieta J, Canary JW,. Derivatization, complexation, and absolute configurational assignment of chiral primary amines: application of exciton-coupled circular dichroism. Chirality 2003; 15: 180-189. (Pubitemid 36163379)
25. Holmes AE, Das D, Canary JW,. Chelation-enhanced circular dichroism of tripodal bisporphyrin ligands. J Am Chem Soc 2007; 129: 1506-1507.
26. Li X, Tanasova M, Vasileiou C, Borhan B,. Fluorinated Porphyrin Tweezer: A powerful reporter of absolute configuration for erythro and threo diols, amino alcohols, and diamines. J Am Chem Soc 2008; 130: 1885-1893. (Pubitemid 351238639)
27. Li X, Burrell CE, Staples RJ, Borhan B,. Absolute configuration for 1,n-glycols: A nonempirical approach to long-range stereochemical determination. J Am Chem Soc 2012; 134: 9026-9029.
28. Waki M, Abe H, Inouye M,. Translation of mutarotation into induced circular dichroism signals through helix inversion of host polymers. Angew Chem Int Ed 2007; 46: 3059-3061. (Pubitemid 46978146)
29. Wezenberg SJ, Salassa G, Escudero-Adan EC, Benet-Buchholz J, Kleij AW,. Effective chirogenesis in a bis(metallosalphen) complex through host-guest binding with carboxylic acids. Angew Chem Int Ed 2011; 50: 713-716.
30. Kim MJ, Choi YR, Jeon H-G, Kang P, Choi M-G, Jeong K-S,. A helically twisted imine macrocycle that allows for determining the absolute configuration of α-amino carboxylates. Chem Commun 2013; 49: 11412-11414.
31. Wolf C, Bentley KW,. Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output. Chem Soc Rev 2013; 42: 5408-5424.
32. Ghosn M, Wolf C,. Chiral amplification with a stereodynamic triaryl probe: assignment of the absolute configuration and enantiomeric excess of amino alcohols. J Am Chem Soc 2009; 131: 16360-16361.
33. Iwaniuk DP, Wolf C,. A Stereodynamic probe providing a chiroptical response to substrate-controlled induction of an axially chiral arylacetylene framework. J Am Chem Soc 2011; 133: 2414-2417.
34. Iwaniuk DP, Wolf C,. Chiroptical sensing of citronellal: Systematic development of a stereodynamic probe using the concept of isostericity. Chem Commun 2012; 48: 11226-11228.
35. Bentley KW, Wolf C,. A stereodynamic chemosensor with selective circular dichroism and fluorescence readout for in situ determination of absolute configuration, enantiomeric excess and concentration of chiral compounds. J Am Chem Soc 2013; 135: 12200-12203.
36. Zhang P, Wolf C,. Sensing of the concentration and enantiomeric excess of chiral compounds with tropos ligand derived metal complexes. Chem Commun 2013; 49: 7010-7012.
37. Bentley KW, Nam YG, Murphy JM, Wolf C,. Chirality sensing of amines, diamines, amino acids, amino alcohols, and α-hydroxy acids with a single probe. J Am Chem Soc 2013; 135: 18052-18055.
38. Nakano K, Hashimoto S, Nakamura M, Kamada T, Nozaki K,. Stereocomplex of poly(propylene carbonate): Synthesis of stereogradient poly(propylene carbonate) by regio- and enantioselective copolymerization of propylene oxide with carbon dioxide. Angew Chem Int Ed 2011; 50: 4868-4871.
39. Baleizão C, Garcia H,. Chiral salen complexes: An overview to recoverable and reusable homogeneous and heterogeneous catalysts. Chem Rev 2006; 106: 3987-4043. (Pubitemid 44560463)
40. Birrell JA, Jacobsen EN,. A Practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols. Org Lett 2013; 78: 2895-2897.
41. III complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols. J Am Chem Soc 2002; 124: 1307-1315. (Pubitemid 34169137)
42. Ford DD, Nielsen LPC, Zuend SJ, Musgrave CB, Jacobsen EN,. Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution. J Am Chem Soc 2013; 135: 15595-15608.
43. Kumar M, Kureshy RI, Shah AK, Das A, Khan NH, Abdi SHR, Bajaj HC,. Asymmetric aminolytic kinetic resolution of racemic epoxides using recyclable chiral polymeric Co(III)-salen complexes: A protocol for total utilization of racemic epoxide in the synthesis of (R)-naftopidil and (S)-propranolol. J Org Chem 2013; 78: 9076-9084.
44. Bredihhina J, Villo P, Andersons K, Toom L, Vares L,. Hydrolytic and aminolytic kinetic resolution of terminal bis-epoxides. J Org Chem 2013; 78: 2379-2385.
45. Mizuno T, Takeuchi M, Shinkai S,. Sugar sensing using chiral salen-Co(II) complexes. Tetrahedron 1999; 55: 9455-9468. (Pubitemid 29333672)
46. Fujii Y, Matsufuru M, Saito A, Tsuchiya S,. The stereochemistry and reactivity of metal-Schiff base complexes. IV. The stereoselectivity of N,N′-ethylenebis(α-methylsalicylideneaminato)cobalt(III) complexes with N-benzyl-L-alanine, N-methyl-L-alanine, and N-benzyl-N-methyl-L-alanine, and the stereospecificity of [1S,2S)-N,N′-1,2- cyclohexylenebis(salicylideneaminato)cobalt(III) complexes toward N-benzyl-L-alanine. Bull Chem Soc Jpn 1981; 54: 2029-2038.
47. Fujii Y, Matsutani K, Kikuchi K,. Formation of a specific coordination cavity for a chiral amino acid by template synthesis of a polymer Schiff base cobalt(III) complex. J Chem Soc Chem Commun 1985; 415-417.
48. Dzygiel P, Reeve TB, Piarulli U, Krupicka M, Tvaroska I, Gennari C,. Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies. Eur J Org Chem 2008; 1253-1264.
49. Kim H-J, Kim W, Lough AJ, Kim BM, Chin J,. A cobalt(III)-salen complex with an axial substituent in the diamine backbone: Stereoselective recognition of amino alcohols. J Am Chem Soc 2005; 127: 16776-16777. (Pubitemid 41772824)
50. Welby J, Rusere LN, Tanski JM, Tyler LA,. Synthesis and crystal structures of mono-, di- and trinuclear cobalt complexes of a salen type ligand. Inorg Chim Acta 2009; 362: 1405-1411.
51. Zhang Y-L, Ruan W-J, Zhao X-J, Wang H-G, Zhu Z-A,. Synthesis and characterization of axial coordination cobalt(III) complexes containing chiral salen ligands. Polyhedron 2003; 22: 1535-1545.
52. Iranmanesh H, Behzad M, Bruno G, Rudbari HA, Nazari H, Mohammadi A, Taheri O,. Cobalt(III) Schiff base complexes derived from mesostilbenediamine: Synthesis, characterization, crystal structure, electrochemistry and antibacterial studies. Inorg Chim Acta 2013; 395: 81-88.
53. Cyriac A, Jeon JY, Varghese JK, Park JH, Choi SY, Chung YK, Lee BY,. Unusual coordination mode of tetradentate Schiff base cobalt(III) complexes. Dalton Trans 2012; 41: 1444-1447.
54. 2 into metal-phenoxide bonds. Green Chem 2013; 15: 1356-1360.