VCD study of α-methylbenzyl amine derivatives: Detection of the unchanged chiral motif

Chirality

Volumn 22, Issue 8, 2010, Pages 754-761

  Merten, Christian ^a   Amkreutz, Marc ^a   Hartwig, Andreas ^a  

^a FRAUNHOFER INSTITUTE FOR MANUFACTURING TECHNOLOGY AND ADVANCED MATERIALS IFAM   (Germany)

Author keywords

Chiral amines; Conformational distribution; Density functional theory; Vibrational circular dichroism

Indexed keywords

ALPHA METHYLBENZYLAMINE DERIVATIVE; BENZYLAMINE DERIVATIVE; BIS(ALPHA METHYLBENZYL)AMINE; N,ALPHA DIMETHYLBENZYLAMINE; N,N,ALPHA TRIMETHYLBENZYLAMINE; UNCLASSIFIED DRUG; 1-PHENETHYLAMINE; PHENETHYLAMINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; DENSITY FUNCTIONAL THEORY; PRIORITY JOURNAL; SPECTROSCOPY; VIBRATION; VIBRATIONAL CIRCULAR DICHROISM; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

CIRCULAR DICHROISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENETHYLAMINES; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 77955138803     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20830     Document Type: Article

References (26)

1. Juaristi E, Escalante J, León-Romo JL, Reyes A. Recent applications of α-phenylethylamine (α-PEA) in the preparation of enantiopure compounds. Part 1: incorporation in chiral catalysts. Part 2: α-PEA and derivatives as resolving agents. Tetrahedron: Asymmetry 1998;9:715-740.
2. Juaristi E, León-Romo JL, Reyes A, Escalante J. Recent applications of a-phenylethylamine (α-PEA) in the preparation of enantiopure compounds. Part 3: α-PEA as chiral auxiliary. Part 4: α-PEA as chiral reagent in the stereodifferentiation of prochiral substrates. Tetrahedron: Asymmetry 1999;10:2441-2495.
3. Bisel P, Fondekar KP, Volk FJ, Frahm AW. Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: bicyclic glutamic acid derivatives. Tetrahedron 2004;60:10541-10545. (Pubitemid 39330638)
4. Siwicka A, Wojtasiewicz K, Leniewski A, Maurin JK, Zawadzka A, Czarnocki Z. (R)-1-phenylethylamine as chiral auxiliary in the diastereoselective synthesis of tetrahydro-β-carboline derivatives. Can J Chem 2007;85:1033-1036. (Pubitemid 351191368)
5. Molnár P, Bombicz P, Varga C, Bereczki L, Székely E, Pokol G, Fogassy E, Simándi B. Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction. Chirality 2009;21:628-636.
6. Ashcroft CP, Challenger S, Clifford D, Derrick AM, Hajikarimian Y, Slucock K, Silk TV, Thomson NM, Williams JR. An efficient and scalable synthesis of the endothelin antagonists UK-350,926 and UK-349,862 using a dynamic resolution process. Org Process Res Dev 2005;9:663-669. (Pubitemid 41422493)
7. Shkolnikova NI, Kutulya LA, Pivnenko NS, Roshal AD, Semenkova GP. New (S)-1-phenylethylamine N-arylidene derivatives as chiral dopants to liquid crystalline systems. Liq Cryst 2007;34:1193-1200.
8. Freedman T, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molcules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758. (Pubitemid 37356644)
9. Stephens PJ, Devlin FJ, Pan JJ. The Determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality 2008;20:643-663.
10. Urbanova M, Setnicka V, Devlin FJ, Stephens PJ. Determination of molecular structure in solution using vibrational circular dichroism spectroscopy: the supramolecular tetramer of S-2,2′-Dimethyl-Biphenyl-6, 6′-dicarboxylic acid. J Am Chem Soc 2005;128:6700-6711. (Pubitemid 40664177)
11. Novy J, Urbanova M. Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG-dC)10 and (dA-dT)10. Biopolymers 2007;94:349-358.
12. Andrushchenko V, Tsankov D, Wieser H. Vibrational circular dichroism spectroscopy and the effects of metal ions on DNA structure. J Mol Struct 2003;661-662:541-560. (Pubitemid 38169088)
13. Wang F, Polavarapu PL, Lebon F, Longhi G, Abbate S, Catellani M. Absolute configuration and conformational stability of (S)-(+)-3-(2-methylbutyl) thiophene and (+)-3,4-Di[(S)-2-methylbutyl)]thiophene and their polymers. J Phys Chem A 2002;106:5918-5923. (Pubitemid 35289919)
14. Monde K, Taniguchi T, Miura N, Vairappan CS, Suzuki M. Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism. Chirality 2006;18:335-339. (Pubitemid 43672682)
15. Tang H-Z, Garland ER, Novak BM, He J, Polavarapu PL, Chen Sun F, Sheiko SS. Helical polyguanidines prepared by helix-sense-selective polymerizations of achiral carbodiimides using enantiopure binaphthol-based titanium catalysts. Macromolecules 2007;40:3575-3580. (Pubitemid 46841913)
16. Kawauchi T, Kumaki J, Kitaura A, Okoshi K, Kusanagi H, Kobayashi K, Sugai T, Shinohara H, Yashima E. Encapsulation of fullerenes in a helical PMMA cavity leading to a robust processable complex with a macromolecular helicity memory. Angew Chem 2008;120:525-529.
17. Nafie LA, Keiderling TA, Stephens PJ. Vibrational circular dichroism. J Am Chem Soc 1976;98:2715-2723.
18. Polavarapu PL, Michalska DF, Neergaard JR, Smith HE. Vibrational circular dichroism of α-phenylethylamine. J Am Chem Soc 1984;106:3378-3380.
19. Accelrys Software Inc. Materials studio release notes, release 4.4. San Diego: Accelrys Software Inc.; 2008.
20. Delley B. An all-electron numerical method for solving the local density functional for polyatomic molecules. J Chem Phys 1990;92:508-517.
21. Perdew JP, Wang Y. Accurate and simple analytic representation of the electron-gas corelation energy. Phys Rev B 1992;45:13244.
22. Gaussian 03, Revision C. 02.Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Wallingford CT: Gaussian, Inc.; 2004.
23. Macleod NA, Butz P, Simons JP, Grant GH, Baker CM, Tranter GE. Structure, electronic circular dichroism and Raman optical activity in the gas phase and solution: a computational and experimental investigation. Phys Chem Chem Phys 2005;7:1432-1440. (Pubitemid 40523981)
24. Solladié-Cavallo A, Marsol C, Pescitelli G, Di Bari L, Salvadori P, Huang X, Fujioka N, Berova N, Cao X, Freedman TB, Nafie LA. (R)-(+)- and (S)-(+)-1-(9-Phenantryl)ethylamine: assignment of absolute configuration by CD tweezer and VCD methods, and difficulties encountered with the CD exciton chirality method. Eur J Org Chem 2002;11:1788-1796.
25. Petrovic AG, Polavarapu PL, Drabowicz J, Lyzwa P, Mikolajczyk M, Wieczorek W, Balinska A. Diastereomers of N-α-phenylethyl-t- butylsulfinamide: absolute configurations and predominant conformations. J Org Chem 2008;73:3120-3129.
26. Polavarapu PL, Fontana LP, Smith HE. Vibrational circular dichroism of phenylcarbinols. A configurational correlation. J Am Chem Soc 1986;108:94-99.