Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2703-2705

  Bertozzi, Fabio ^a,b   Pineschi, Mauro ^b   Macchia, Franco ^b   Arnold, Leggy A ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF PISA   (Italy)

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ARTICLE;

EID: 0001701335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026220u     Document Type: Article

References (25)

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2. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
3. (a) de Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374.
4. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620.
5. (c) Imbos, R.; Brilman, M. H. G.; Pineschi, M.; Feringa, B. L. Org. Lett. 1999, 1, 623.
6. Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104.
7. Naasz, R.; Arnold; L. A.; Minnaard; A. J.; Feringa, B. L. Angew. Chem., Int. Ed. Engl. 2001, 40, 927.
8. Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Feringa, B. L. Angew. Chem., Int. Ed. Engl. 2001, 40, 930 and references therein.
9. (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
10. (b) Imbos, R., Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
11. For reviews, see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 790, 1.
12. (b) Lautens, M. Synlett 1993, 177.
13. Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532.
14. (a) Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170.
15. (b) Lautens, M.; Fagnou, K.; Rovis, T. J. Am. Chem. Soc. 2000, 122, 5650.
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17. (a) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2001, 123, 6834.
18. (b) Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2000, 122, 1804. For an alternative enantioselective ring opening, see: Millward, D. B.; Sammis, G.; Waymouth, R. M. J. Org. Chem. 2000, 65, 3902.
19. (b) Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2000, 122, 1804. For an alternative enantioselective ring opening, see: Millward, D. B.; Sammis, G.; Waymouth, R. M. J. Org. Chem. 2000, 65, 3902.
20. Lautens, M.; Smith, A. C.; Abd-El-Aziz, A. S.; Huboux, A. H. Tetrahedron Lett. 1990, 31, 3253.
21. 2 (1.0 equiv) afforded syn-4a (42%) and α-naphthol (24%).
22. 2, and diglyme. In all cases, complex reaction mixtures containing racemic syn-adduct 4a and only trace amounts of anti-adduct 3a were obtained.
23. 11
24. For a typical procedure, see the Supporting Information.
25. Chiral phosphoramidite 5 afforded compounds 11-15 with a slight decrease (2-3%) in stereoselectivity.