Organolithium additions to styrene derivatives - III. Enantioselective routes to 2-arylalkanoic acids

Tetrahedron Asymmetry

Volumn 8, Issue 5, 1997, Pages 665-668

  Xudong, Wei ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLALIPHATIC CARBOXYLIC ACID; STYRENE DERIVATIVE;

ARTICLE; CARBOXYLATION; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343923544     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00032-3     Document Type: Article

References (24)

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2. Part 2: Wei, X.; Taylor, R. J. K. Tetrahedron Lett., 1996, 37, 4209.
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10. Voyer, N.; Roby, J. Tetrahedron Lett., 1995, 36, 6627 and references therein; for key references in related non-benzylic systems see Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc., 1996, 118, 715; Kaiser, B.; Hoppe, D. Angew. Chem., Int. Ed. Engl., 1995, 34, 323.; Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. II, 1995, 1721 and references therein.
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12. Voyer, N.; Roby, J. Tetrahedron Lett., 1995, 36, 6627 and references therein; for key references in related non-benzylic systems see Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc., 1996, 118, 715; Kaiser, B.; Hoppe, D. Angew. Chem., Int. Ed. Engl., 1995, 34, 323.; Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. II, 1995, 1721 and references therein.
13. All products were analysed spectroscopically and new compounds were further characterised by HRMS.
14. Guette, J. P.; Lacombe, L.; Horeau, A. C. R. Acad. Sci. Ser. C, 1968, 276, 166 and Horeau, A.; Guette, J. P. C. R. Acad. Sci. Ser. C, 1968, 276, 166. For a review see Pirkle, W. H.; Hoover, D. J. Top. Stereochem., 1982, 13, 263.
15. Guette, J. P.; Lacombe, L.; Horeau, A. C. R. Acad. Sci. Ser. C, 1968, 276, 166 and Horeau, A.; Guette, J. P. C. R. Acad. Sci. Ser. C, 1968, 276, 166. For a review see Pirkle, W. H.; Hoover, D. J. Top. Stereochem., 1982, 13, 263.
16. Guette, J. P.; Lacombe, L.; Horeau, A. C. R. Acad. Sci. Ser. C, 1968, 276, 166 and Horeau, A.; Guette, J. P. C. R. Acad. Sci. Ser. C, 1968, 276, 166. For a review see Pirkle, W. H.; Hoover, D. J. Top. Stereochem., 1982, 13, 263.
17. Rogan, M. M.; Altria, K. D.; Goodall, D. M. Chirality, 1994, 6, 25; Chankvetadze, B.; Endresz, G.; Blaschke, G. Chem. Soc. Rev., 1996, 25, 141. Ee's determined on a Beckman 2100 instrument.
18. Rogan, M. M.; Altria, K. D.; Goodall, D. M. Chirality, 1994, 6, 25; Chankvetadze, B.; Endresz, G.; Blaschke, G. Chem. Soc. Rev., 1996, 25, 141. Ee's determined on a Beckman 2100 instrument.
19. 20=-18 (c=1, EtOH)} as might be expected from related examples (see ref. 4b).
20. The substituted styrenes were prepared by standard procedures such as Wittig homologation of the corresponding aldehyde or by trapping 2-bromomagnesiostyrene.
21. 9
22. We do not yet know the absolute configurations of the predominant enantiomers featured in Table 2.
23. 2 styrenes were also investigated; amide addition giving a butylketone (ca. 60%) occurred in the former case whereas the carbamate gave a complex product mixture.
24. Page, P. C. B.; McKenzie, M. J.; Buckle, D. R. J. Chem. Soc., Perkin Trans. I, 1995, 2673 and references therein.