Ultra-remote stereocontrol by conformational communication of information along a carbon chain

Nature

Volumn 431, Issue 7011, 2004, Pages 966-971

  Clayden, Jonathan ^a   Lund, Andrew ^a   Vallverdú, Lluís ^a   Helltwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CONFORMATIONS; DATA TRANSFER; MOLECULAR STRUCTURE; PROTEINS; REMOTE CONTROL;

ALLOSTERIC PROTEINS; CONFORMATIONAL CHANGES; ULTRA-REMOTE STEREOCONTROL;

MOLECULAR DYNAMICS;

CARBON;

BIOLOGY;

ALLOSTERISM; ARTICLE; BINDING SITE; CHEMICAL MODEL; CHEMICAL REACTION KINETICS; CONFORMATION; CONFORMATIONAL TRANSITION; INFORMATION PROCESSING; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; RECEPTOR BINDING; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 7244228083     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/nature02933     Document Type: Article

References (28)

1. Krauss, G. Biochemistry of Signal Transduction and Regulation (Wiley-VCH, Weinheim, 1999).
2. Perutz, M. Mechanisms of Cooperativity and Allosteric Regulation in Proteins (Cambridge Univ. Press, Cambridge, 1990).
3. Eliel, E. L. & Wilen, S. H. Stereochemistry of Organic Compounds Ch. 12 (Wiley, New York, 1994).
4. Mikami, K., Shimizu, M., Zhang, H.-C. & Maryanoff, B. E. Acydic stereocontrol between remote atom centers via intramolecular and intermolecular stereo-communication. Tetrahedron 57, 2917-2951 (2001).
5. Linnane, P., Magnus, N. & Magnus, P. Induction of molecular asymmetry by a remote chiral group. Nature, 799-801 (1997).
6. Clayden, J., Mitjans, D. & Youssef, L. H. Lithium-sulfoxide-lithium exchange for the asymmetric synthesis of atropisomers under thermodynamic control. J. Am. Chem. Soc. 124, 5266-5267 (2002).
7. Clayden, J. & Lai, L. W. (-)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control. Tetrahedron Lett. 42, 3163-3166 (2001).
8. Clayden, J., Lai, L. W. & Helliwell, M. Using amide conformation to "project" the stereochemistry of a (-)-ephedrine-derived oxazolidine: a pair of pseudoenantiomeric chiral amido-phosphine ligands. Tetrahedron 12, 695-698 (2001).
9. Clayden, J. & Lai, L. W. Enantioselective synthesis of atropisomeric amides by dynamic resolution: thermodynamic control with a proline-derived diamine resolving agent. Angew. Chem. Intl Edn 38, 2556-2558 (1999).
10. Clayden, J., Pink, J. H. & Yasin, S. A. Conformationally interlocked amides: remote asymmetric induction by mechanical transfer of stereochemical information. Tetrahedron Lett. 39, 105-108 (1998).
11. Clayden, J., Kenworthy, M. N. & Youssef, L. H. Axial chirality in xanthene-4,5-dicarboxamides: 1,9-stereocontrol mediated by remote interactions between conformationally constrained amide groups. Tetrahedron Lett. 41, 5171-5174 (2000).
12. Clayden, J., Lund, A. & Youssef, L. H. Conformational preference and remote (1,10) stereocontrol in biphenyl-2,2′-dicarboxamides. Org. Lett. 3, 4133-4136 (2001).
13. Clayden, J. Stereocontrol with rotationally restricted amides. Synlett, 810-816 (1998).
14. Krauss, R. & Koert, U. Molecular signal transduction by conformational transmission. Synlett, 598-608 (2003).
15. Balzani, V., Credi, A. & Venturi, M. The bottom-up approach to molecular-level devices and machines. Chem. Eur. J. 8, 5524-5542 (2002).
16. Sauvage, J.-P. Transition-metal containing rotaxanes and catenanes in motion: toward molecular machines and motors. Acc. Chem. Res. 31, 611-619 (1998).
17. Cuyegkeng, M. A. & Mannschreck, A. Chromatographic separation of enantiomers and barriers to enantiomerizatton of axially chiral aromatic carboxamides. Chem. Ber. 120, 803-809 (1987).
18. Bowles, P. et al. Atroposelectivity in the reactions of ortholithiated tertiary amides with aldehydes. J. Chem. Soc. Perkin Trans, 1, 2607-2616 (1997).
19. Ahmed, A. et al. Barriers to rotation about the chiral axis of tertiary aromatic amides. Tetrahedron 54, 13277-13294 (1998).
20. Snieckus, V. Directed ortho metalation. Tertiary amide and O-carhamate directors in synthetic strategies for polysubstituted aromatics. Chem. Rev. 90, 879-933 (1990).
21. Yin, J., Rainka, M. P., Zhang, X.-X. & Buchwald, S. L. A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: novel ligand coordination. J. Am. Chem. Soc. 124, 1162-1163 (2002).
22. Clayden, J., Lai, L. W. & Helliwell, M. Dynamic resolution of atropisomeric amides using proline-derived imidazolidines and ephedrine-derived oxazolidines, Tetrahedron 60, 4399-4412 (2004).
23. Clayden, J., McCarthy, C., Westlund, N. & Frampton, C. S. Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: chelation and non-chelation control. J. Chem. Soc. Perkin Trans. 1, 1363-1378 (2000).
24. Date, M. et al. Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen- 2-ols with an oligoether tether as the 2′-substituent: application to the synthesis of (-)-malyngolide. J. Chem. Soc. Perkin Trans, 1, 645-653 (2001).
25. Tamai, Y. et al. Efficient 1,8- to 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary. J. Chem. Soc. Perkin Trans. 1, 1141-1142 (1999).
26. Magnus, N. & Magnus, P. 1,13- and 1,14-asymmetric induction; remote control. Tetrahedron Lett. 38, 3491-3494 (1997).
27. Heinemann, C. & Demuth, M. Short biomimetic synthesis of a steroid by photoinduced electron transfer and remote asymmetric induction. J. Am. Chem. Soc. 121, 4894-4895 (1999).
28. Agami, C. & Rizk, T. Kinetic control of asymmetric induction during oxazolidine formation from (-)-ephedrine and aromatic aldehydes. Tetrahedron 41, 537-540 (1985).