Chiral derivatives of 2-(1-naphthyl)-2-phenylacetic acid

Chirality

Volumn 16, Issue 9, 2004, Pages 652-660

  Vávra, Jan ^a   Vodička, Petr ^b   Streinz, Ludvík ^b   Budesinsky, Milos ^b   Koutek, Bohumír ^b   Ondráček, Jan ^c   Císařová, Ivana ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c INSTITUTE OF MOLECULAR GENETICS   (Czech Republic)

Author keywords

Chiral analysis; Derivatization; Enantiomers; NMR; Separation

Indexed keywords

2 (1 NAPHTHYL) 2 PHENYLACETIC ACID; ALKYL GROUP; NAPHTHYL GROUP; PHENYL GROUP; PHENYLACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTALLOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIMETRY; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SPECTROSCOPY; STEREOISOMERISM;

EID: 7044229832     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20087     Document Type: Article

References (27)

1. Eliel EL, Wilen SH, Mander LN. Stereochemistry of Organic Compounds. New York: John Wiley & Sons; 1994. p. 101-147.
2. Seco JM, Quiňoá E, Riguerra AR. The assignment of absolute confoguration by NMR. Chem Rev 2004;104:17-117. Dale JA, Dull DL, Mosher HS. α-Methoxy-α-trifluoromethylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2549.
3. Seco JM, Quiňoá E, Riguerra AR. The assignment of absolute confoguration by NMR. Chem Rev 2004;104:17-117. Dale JA, Dull DL, Mosher HS. α-Methoxy-α-trifluoromethylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2549.
4. Bodkin JA, Humphries EJ, McLeod MD. The total synthesis of (-)-tetrahydrolipstatin. Tetrahedron Lett 2003;14:2869-2872.
5. Kiho T, Nakayama M, Kogen H. Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A(5). Tetrahedron 2003;39:1685-1697.
6. Moreno-Dorado F, Guerra FM, Ortega MJ, Zubia E, Massanet GM. Enantioselective synthesis of arylmethoxyacetic acid derivatives. Tetrahedron Asymmetry 2003;14:503-510.
7. Couche E, Fkyerat A, Tabachi R. Asymmetric synthesis of the cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones. Helv Chim Acta 2003;86:210-221.
8. Bugni TS, Bernan AS, Greenstein M, Janso JE, Maiese WM, Mayne CL, Ireland CM. Brocaenols A-C: novel polyketides from a marine-derived Penicillium brocae. J Org Chem 2003;68:2014-2017.
9. Carletti I, Long C, Funel C, Armade P. Yardenone A and B: new cytotoxic triterpenes from the Indian Ocean sponge Axinella cf bidderi. J Nat Prod 2003;66:25-29.
10. McMillan JB, Molinski TF. Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula. Organic Lett 2002;4:1535-1538.
11. Moon SS, McMillan JB, Olmstead MM, Ta TA, Pescah IN, Molinski TF. (+)-7S-hydroxyxestospongin A from the marine sponge Xestospongia sp and absolute configuration of (+)-xestospongin D. J Nat Prod 2002;65:249-254.
12. Shimbo K, Tsuda M, Izui N, Kobayashi J. Amphidinolide W, a new 12-membered macrolide from dinoflagellate Amphidinium sp. J Org Chem 2002;67:1020-1023.
13. Růžička J, Streinz L, Wimmer Z, Rejzek M, Zarevúcka M, Koutek B, Lešetický L. Chlorofluoroacetic acid derivatives of sterically hindered chiral alcohols. J Chem Res 1998;3401-3409.
14. Růžička J, Streinz L, Šaman D, Havlas Z, Wimmer Z, Zarevúcka M, Koutek B, Lešetický L. Chlorofluoroacetic acid as a highly versatile derivatizing agent: assignment of stereochemistry to esters of chiral alcohols. Collect Czech Chem Commun 2000;65:695-707.
15. Brook AG. The configuration of (+)-methyl-α-naphthylphenylmethane, -silane, and -germane. J Am Chem Soc 1963;85:3051-3052.
16. Vávra J. PhD dissertation. Chiral derivatization with 2-(1-naphthyl)-2-phenylacetic acid. Charles University, Prague, 2002.
17. Vávra J, Streinz L, Vodička P, Buděší nský M, Koutek B. An effective hydrolysis of crowded chiral esters. SynLett 2002;11:1886-1888.
18. Shi X, Lea WS, Meinwald J. Assignment of absolute stereochemistry to an insect pheromone by chiral amplification. Bioorg Med Chem 1996;4:297-303.
19. Trost BM, Bunt RC, Pulley SR. On the use of O-methylmandelic acid for the establishment of absolute-configuration of alpha-chiral primary amines. J Org Chem 1994;59:4202-4205.
20. Seco JM, Latypov S, Quiňoá E, Riguerra AR. New chirality recognizing reagents for the determination of absolute stereochemistry and enantiomeric purity by NMR. Tetrahedron Lett 1994;35:2921-2924.
21. Kusumi T, Takahashi H, Xu P, Fukushima T, Asakawa Y, Hashimoto T, Kan Y. New chiral anisotropic reagents, NMR tools to elucidate the absolute- configurations of long-chain organic-compounds. Tetrahedron Lett 1994;35:4397-4400.
22. Ichikawa A, Yasuda T, Wakamura S. Absolute configuration of sex pheromone for Tea Tussock Moth, Euproctis pseudoconspersa (Strand) via synthesis of (R)- and (S)-10,14-dimethyl-1-pentadecyl isobutyrates. J Chem Ecol 1995;21:627-634.
23. Svatoš A, Valterová I, Šaman D, Vrkoč J. Direct esterification of 2-methoxy-2- 2-phenyl-3,3,3-trifluoropropionic acid - A reinvestigation. Collect Czech Chem Commun 1990;55:485-490.
24. Mori K, Inunaka M. Pheromone synthesis. 65. Synthesis of all of the 4 energetically possible stereoisomers of 7-ethyl-2-methyl-1,6-dioxaspiro[4.5] decane - a pheromone produced by bees paravespura-vulgaris L and Andrena-haemorrhoa F. Tetrahedron 1984;40:3471-3479.
25. Streinz L, Svatoš A, Vrkoč J, Meinwald JJ. Preparation of chlorofluoroacetic acid for the analysis of chiral alcohols. J Chem Soc Perkin Trans 1 1994;3509-3512.
26. Hose DRJ, Mahon MF, Malloy KC, Rynham T, Wills M. Asymmetric synthesis of amines using a chiral, non-racemic, benzylidene sulfinamide derived from a recoverable precursor. J Chem Soc Perkin Trans 1 1996;7:691-703.
27. Kusumi T, Fukushima T, Ohtani I, Kakisawa H. Elucidation of the absolute- configurations of amino-acids and amines by the modified Mosher method. Tetrahedron Lett 1991;32:2939-2942.