Chirality Sensing with Stereodynamic Biphenolate Zinc Complexes

Chirality

Volumn 27, Issue 10, 2015, Pages 700-707

  Bentley, Keith W ^a   De Los Santos, Zeus A ^a   Weiss, Mary J ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

chemosensor; chiral amplification; circular dichroism; enantioselective analysis; stereolabile zinc complex

Indexed keywords

DIETHYLZINC; ETHER; ZINC COMPLEX;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTALLOGRAPHY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; PARTICLE SIZE; PRIORITY JOURNAL; SONOGASHIRA REACTION;

EID: 84942828430     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22489     Document Type: Article

References (51)

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. Wolf C, (Ed) Dynamic stereochemistry of chiral compounds. RSC Publishing: Cambridge, UK; 2008.
3. Leung D, Kang SO, Anslyn EV,. Rapid determination of enantiomeric excess: a focus on optical approaches. Chem Soc Rev 2012; 41: 448-479.
4. Wolf C, Bentley KW,. Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output. Chem Soc Rev 2013; 42: 5408-5424.
5. 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.
6. 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.
7. For a review of supramolecular sensors, Hembury GA, Borovkov VV, Inoue Y,. Chirality-sensing supramolecular systems. Chem Rev 2008; 108: 1-73.
8. 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.
9. Mazaleyrat JP, Wright K, Gaucher A, Toulemonde N, Wakselman M, Oancea S, Peggion C, Formaggio F, Setnicka V, Keiderling TA, Toniolo C,. Induced axial chirality in the biphenyl core of the Cα-tetrasubstituted α-amino acid residue Bip and subsequent propagation of chirality in (Bip)n/Val oligopeptides. J Am Chem Soc 2004; 126: 12874-12879.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. Berova N, Pescitelli G, Petrovic AG, Proni G,. Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts. Chem Commun 2009; 5958-5980.
25. 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.
26. 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.
27. 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.
28. 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.
29. Dragna JM, Gade AM, Tran L, Lynch VM, Anslyn EV,. Chiral amine enantiomeric excess determination using self-assembled octahedral Fe(II)-imine complexes. Chirality 2015; 27: 294-298.
30. 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.
31. Holmes AE, Das D, Canary JW,. Chelation-enhanced circular dichroism of tripodal bisporphyrin ligands. J Am Chem Soc 2007; 129: 1506-1507.
32. Joyce LA, Sherer EC, Welch CJ,. Imine-based chiroptical sensing for analysis of chiral amines: from method design to synthetic application. Chem Sci 2014; 5: 2855-2861.
33. 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.
34. 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.
35. Anyika M, Gholami H, Ashtekar KD, Acho R, Borhan B,. Point-to-axial chirality transfer-a new probe for "sensing" the absolute configuration of monoamines. J Am Chem Soc 2014; 136: 550-553.
36. 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.
37. Ghosn M, Wolf C,. Enantioselective CD analysis of amino acids based on chiral amplification with a stereodynamic probe. Tetrahedron 2010; 66: 3989-3994.
38. Ghosn M, Wolf C,. Synthesis, conformational stability and asymmetric transformation of atropisomeric 1,8-bisphenolnaphthalenes. J Org Chem 2011; 76: 3888-3897.
39. Ghosn M, Wolf C,. Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene. Tetrahedron 2011; 67: 6799-6803.
40. 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.
41. Bentley KW, Wolf C,. Comprehensive chirality sensing: Development of stereodynamic probes with a dual (chir)optical response. J Org Chem 2014; 79: 6517-6531.
42. Cort AD, Gasparrini F, Lunazzi L, Mandolini L, Mazzanti A, Pasquini C, Pierini M, Rompietti R, Schiaffino L,. Stereomutations of atropisomers of sterically hindered salophen ligands. J Org Chem 2005; 70: 8877-8883.
43. 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.
44. 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. DOI: 10.1021/ja410428b#-blank.
45. Irfanoglu B, Wolf C,. Circular dichroism sensing of chiral compounds using an achiral metal complex as probe. Chirality 2014; 26: 379-384.
46. Peng R, Lin L, Cao W, Guo J, Liu X, Feng X,. A racemic N,N -dioxide-iron(III) complex chemosensor for determination of enantiomeric excess, concentration and identity of hydroxy carboxylic acids with circular dichroism and fluorescence responses. Tetrahedron Lett 2015; 56: 3882-3885.
47. 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.
48. Iwaniuk DP, Wolf C,. Enantioselective sensing of amines based on [1+1]-, [2+2]-, and [1+2]-condensation with fluxional arylacetylene-derived dialdehydes. Org Lett 2011; 13: 2602-2605.
49. 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.
50. Iwaniuk DP, Bentley KW, Wolf C,. Enantioselective sensing of chiral amino alcohols with a stereodynamic arylacetylene-based probe. Chirality 2012; 24: 584-589.
51. Alabugin IV, Gilmore K, Patil S, Manoharan M, Kovalenko SV, Clark RJ, Ghiviriga I,. Radical cascade transformations of tris(o-aryleneethynylenes) into substituted benzo[a]indeno[2,1-c]fluorenes. J Am Chem Soc 2008; 130: 11535-11545.