Efficient Asymmetric Synthesis of 2,6-Disubstituted 2H-Dihydropyrans via a Catalytic Hetero-Diels-Alder/Allylboration Sequence

Advanced Synthesis and Catalysis

Volumn 345, Issue 11, 2003, Pages 1215-1219

  Deligny, Michael ^a   Carreaux, François ^a   Toupet, Loïc ^a   Carboni, Bertrand ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Allylboration; Asymmetric catalysis; Boronic esters; Chromium complex; Dihydropyrans; Hetero Diels Alder

Indexed keywords

3 BORYLACROLEIN; ACROLEIN DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0347653707     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303127     Document Type: Article

References (32)

1. Comprehensive Asymmetric Catalysis, Vols. 1-3, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer: Berlin, 1999; K. A. Jorgensen, Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
2. Comprehensive Asymmetric Catalysis, Vols. 1-3, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer: Berlin, 1999; K. A. Jorgensen, Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
3. D. S. Matteson, Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
4. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
5. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
6. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
7. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
8. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
9. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
10. For selected recent references related to alkenyl- and dienylboronic esters, see: a) G. C. Micalizio, S. L. Schreiber, Angew. Chem. Int. Ed. 2002, 41, 3272-3276; b) G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; c) E. Tyrrell, P. Brookes, Synthesis 2003, 469-483; d) C. J. Chapman, C. G. Frost, Adv. Synth. Cat. 2003, 345, 353-355; e) S. J. Patel, T. F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364-1367; f) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235; g) J. Uenishi, K. Matsui, A. Wada, Tetrahedron Lett. 2003, 44, 3093-3096.
11. A. Suzuki, H. C. Brown, Organic Syntheses via Boranes, Aldrich Chemical Company, Milwaukee, USA, 2003, Vol. 3.
12. For cyclopropanations of optically active boronates, see: a) I. E. Marko, T. Kumamoto, T. Giard, Adv. Synth. Catal. 2002, 344, 1063-1067; b) J. E. A Luithle, J. Pietruszka, Eur. J. Org. Chem. 2000, 2557-2562; c) Pietruszka, J.; Witt, A. J. Chem. Soc. Perkin Trans. 1 2000, 4293-4300 and references cited therein.
13. For cyclopropanations of optically active boronates, see: a) I. E. Marko, T. Kumamoto, T. Giard, Adv. Synth. Catal. 2002, 344, 1063-1067; b) J. E. A Luithle, J. Pietruszka, Eur. J. Org. Chem. 2000, 2557-2562; c) Pietruszka, J.; Witt, A. J. Chem. Soc. Perkin Trans. 1 2000, 4293-4300 and references cited therein.
14. For cyclopropanations of optically active boronates, see: a) I. E. Marko, T. Kumamoto, T. Giard, Adv. Synth. Catal. 2002, 344, 1063-1067; b) J. E. A Luithle, J. Pietruszka, Eur. J. Org. Chem. 2000, 2557-2562; c) Pietruszka, J.; Witt, A. J. Chem. Soc. Perkin Trans. 1 2000, 4293-4300 and references cited therein.
15. For 1,3-cycloadditions of optically active boronates and boratranes, see: a) B. Jiang, A. Zhang, Y. Kan, Chin. J. Chem. 1999, 17, 293-299; b) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 2000, 41, 4229-4233; c) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 1998, 39, 8513-8516 and references cited therein.
16. For 1,3-cycloadditions of optically active boronates and boratranes, see: a) B. Jiang, A. Zhang, Y. Kan, Chin. J. Chem. 1999, 17, 293-299; b) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 2000, 41, 4229-4233; c) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 1998, 39, 8513-8516 and references cited therein.
17. For 1,3-cycloadditions of optically active boronates and boratranes, see: a) B. Jiang, A. Zhang, Y. Kan, Chin. J. Chem. 1999, 17, 293-299; b) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 2000, 41, 4229-4233; c) C. D. Davies, S. P. Marsden, E. S. E. Stokes, Tetrahedron Lett. 1998, 39, 8513-8516 and references cited therein.
18. For Diels-Alder reactions of optically active boronates, see: a) P. Y. Renard, J. Y Lallemand, Tetrahedron Asymmetry 1996, 7, 2523-2524; b) A. Zhang, Y. Kan; B. Jiang, Tetrahedron 2001, 57, 2305-2309; c) J. Mortier, M. Vaultier, B. Plunian, L. Toupet, Heterocycles 1999, 50, 703-711; d) G. Lorvelec, M. Vaultier, Tetrahedron Lett. 1998, 39, 5185-5188; e) B. B. Toure, H. R. Hoveyda, J. Tailor, A. Ulaczyk Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474 and references cited therein.
19. For Diels-Alder reactions of optically active boronates, see: a) P. Y. Renard, J. Y Lallemand, Tetrahedron Asymmetry 1996, 7, 2523-2524; b) A. Zhang, Y. Kan; B. Jiang, Tetrahedron 2001, 57, 2305-2309; c) J. Mortier, M. Vaultier, B. Plunian, L. Toupet, Heterocycles 1999, 50, 703-711; d) G. Lorvelec, M. Vaultier, Tetrahedron Lett. 1998, 39, 5185-5188; e) B. B. Toure, H. R. Hoveyda, J. Tailor, A. Ulaczyk Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474 and references cited therein.
20. For Diels-Alder reactions of optically active boronates, see: a) P. Y. Renard, J. Y Lallemand, Tetrahedron Asymmetry 1996, 7, 2523-2524; b) A. Zhang, Y. Kan; B. Jiang, Tetrahedron 2001, 57, 2305-2309; c) J. Mortier, M. Vaultier, B. Plunian, L. Toupet, Heterocycles 1999, 50, 703-711; d) G. Lorvelec, M. Vaultier, Tetrahedron Lett. 1998, 39, 5185-5188; e) B. B. Toure, H. R. Hoveyda, J. Tailor, A. Ulaczyk Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474 and references cited therein.
21. For Diels-Alder reactions of optically active boronates, see: a) P. Y. Renard, J. Y Lallemand, Tetrahedron Asymmetry 1996, 7, 2523-2524; b) A. Zhang, Y. Kan; B. Jiang, Tetrahedron 2001, 57, 2305-2309; c) J. Mortier, M. Vaultier, B. Plunian, L. Toupet, Heterocycles 1999, 50, 703-711; d) G. Lorvelec, M. Vaultier, Tetrahedron Lett. 1998, 39, 5185-5188; e) B. B. Toure, H. R. Hoveyda, J. Tailor, A. Ulaczyk Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474 and references cited therein.
22. For Diels-Alder reactions of optically active boronates, see: a) P. Y. Renard, J. Y Lallemand, Tetrahedron Asymmetry 1996, 7, 2523-2524; b) A. Zhang, Y. Kan; B. Jiang, Tetrahedron 2001, 57, 2305-2309; c) J. Mortier, M. Vaultier, B. Plunian, L. Toupet, Heterocycles 1999, 50, 703-711; d) G. Lorvelec, M. Vaultier, Tetrahedron Lett. 1998, 39, 5185-5188; e) B. B. Toure, H. R. Hoveyda, J. Tailor, A. Ulaczyk Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474 and references cited therein.
23. [7e]
24. M. Deligny, F. Carreaux, B. Carboni, L. Toupet, G. Dujardin, Chem. Commun. 2003, 276-277.
25. K. Gademan, D. E.; Chavez, E. N. Jacobsen, Angew. Chem. Int. Ed. 2002, 41, 3059-3061.
26. During the preparation of our manuscript, very similar results were reported by Hall and Gao: X. Gao, D. G., Hall, J. Am. Chem. Soc. 2003, 125, 9308-9309.
27. 3 (δ = 1.09 (4R) and 1.12 ppm (4S)).
28. M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett. 1987, 28, 4169-4172; J. Y. Lallemand, Y. Six, L. Ricard, Eur. J. Org. Chem. 2002, 503-513 and references cited therein.
29. M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett. 1987, 28, 4169-4172; J. Y. Lallemand, Y. Six, L. Ricard, Eur. J. Org. Chem. 2002, 503-513 and references cited therein.
30. -1, F(000) = 540, T = 293 K. The absolute configuration is unambiguously confirmed (Flack parameter=-0.02(9)). The two molecules of the asymmetric unit are independent and have the same absolute configuration. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 218262. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code (+44)-1223-336-033; E-mail: deposit@ccdc.cam.ac.uk].
31. Results reported by Hall and Gao showed that a one-pot transformation is possible provided that less catalyst (0.5%) and molecular sieves were used.
32. Y. Kobayashi, Y. Takemoto, T. Kamijo, H. Harada, Y. Ito, S. Terashima, Tetrahedron. 1992, 48, 1853-1868.