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For a collection of excellent reviews: a) Chem. Rev. 2000, 100, 1683-1890 (special issue: Photochromism: Memories and Switches);
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b) P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi, D. J. Williams, J Am. Chem. Soc 1999, 121, 3951-3957;
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a) S. Shinkai in Molecular Switches (Ed.: B. Feringa), Wiley-VCH, Weinheim, 2001, p. 281;
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Koert, U.1
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studies with substituted cyclohexanes: b) M. Raban, D. L. Burch, E. R. Hortelano, D. Durocher, D. Kost, J. Org. Chem 1994, 59, 1283-1287;
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c) V. V. Samoshin, O. A. Zelenkina, I. V. Yartseva, N. S. Zefirov, Zh. Org. Khim. 1987, 23, 2244-2245;
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Samoshin, V.V.1
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d) V. V. Samoshin, V. A. Chertkov, L. P. Vaatlina, E. K. Dobretsova, N. A. Simonov, L. P. Katorsky, D. E. Gremyachinsky, H.-J. Schneider, Tetrahedron Lett. 1996, 37, 3981-3984;
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a) H.-G. Weinig, R. Krauss, M. Seydack, J. Bendig, U. Koert, Chem. Eur. J. 2001, 7, 2075-2088;
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Weinig, H.-G.1
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b) R. Krauss, H.-G. Weinig, M. Seydack, J. Bendig, U. Koert, Angew. Chem. 2000, 112, 1905-1908; Angew. Chem. Int. Ed. 2000, 39, 1835-1837;
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Angew. Chem.
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Krauss, R.1
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b) R. Krauss, H.-G. Weinig, M. Seydack, J. Bendig, U. Koert, Angew. Chem. 2000, 112, 1905-1908; Angew. Chem. Int. Ed. 2000, 39, 1835-1837;
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c) J. Beminger, R. Krauss, H.-G. Weinig, U. Koert, B. Ziemer, K. Harms, Eur. J. Org. Chem. 1999, 875-884.
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e) V. A. Palyulin, S. V. Emets, V. A. Chertkov, C. Kasper, H.-J. Schneider, Eur. J. Org. Chem. 1999, 3479-3482;
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f) J. N. H. Reek, H. Engelkamp, A. E. Rowan, J. A. A. W. Elemans, R. J. M. Nolte, Chem. Eur. J. 1998, 4, 716-722.
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Other examples for the (nonconformative) coupling of molecular switches: F. M. Raymo, S. Giordani, Org. Lett. 2001, 3, 3475-3478.
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(Eds.: W. Bartmann, B. M. Trost), Verlag Chemie, Weinheim
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The concept of macrocyclic stereocontrol was used before in the total synthesis of macrolide natural products: a) "Selectivity-A Goal for Synthetic Efficiency": W. C. Still, Workshop Conferences Hoechst, Vol. 14 (Eds.: W. Bartmann, B. M. Trost), Verlag Chemie, Weinheim, 1983;
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b) G. Quinkert, N. Heim, J. Glenneberg, U. M. Billhardt, V. Autze, J. W. Bats, G. Dürner, Angew. Chem. 1987, 99, 363-365; Angew. Chem. Int. Ed. Engl. 1987, 26, 362-364.
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b) G. Quinkert, N. Heim, J. Glenneberg, U. M. Billhardt, V. Autze, J. W. Bats, G. Dürner, Angew. Chem. 1987, 99, 363-365; Angew. Chem. Int. Ed. Engl. 1987, 26, 362-364.
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K. Furuta, K. Iwanaga, H. Yamamoto, Tetrahedron Lett. 1986, 27, 4507-4510. The stereoselectivity was determined and the stereochemistry of the reaction product was assigned after the reductive cleavage of the menthyl ester. See the Supporting Information for details.
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a) S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 106, 2290-2292;
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a) S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410-2412; Angew. Chem. Int. Ed. Engl. 1994, 106, 2290-2292;
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b) J.-L. Montchamp, F. Tian, M. E. Hart, J. W. Frost, J. Org. Chem. 1996, 61, 3897-3899.
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37
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0141675373
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note
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The switch of the C6 and C7 substituents into axial positions was verified by inspection of the coupling pattern in the DQF-COSY spectrum; the small coupling constant for H6 and H7 is characteristic for bisequatorial protons.
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38
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0542373936
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Review: a) V. Balzani, M. Gomez-Lopez, J.-F. Stoddart, Acc. Chem. Res. 1998, 31, 405-414;
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Balzani, V.1
Gomez-Lopez, M.2
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Kelly, T.R.1
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c) N. Koumura, R. W. J. Zijlstra, R. A. van Delde, N. Harada, B. L. Feringa, Nature 1999, 401, 152-154;
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Koumura, N.1
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Feringa, B.L.5
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