Stereoselective synthesis of 1,4-bifunctional compounds by regioselective Pd-catalyzed allylic substitution reaction

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2177-2180

  Maezaki, Naoyoshi ^a   Hirose, Yuki ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHIRALITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3142703661     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049374d     Document Type: Article

References (34)

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3. For application of olefins flanking two stereogenic centers to a synthesis of natural products, see: Block, O.; Klein, G.; Altenbach, H.-J.; Brauer, D. J. J. Org. Chem. 2000, 65, 716-721. Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993-3005. Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655-12656. Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694-9696. Takeda, K.; Kaji, E.; Konda, Y.; Sato, N.; Nakamura, H.; Miya, N.; Morizane, A.; Yanagisawa, Y.; Akiyama, A.; Zen, S.; Harigaya, Y. Tetrahedron Lett. 1992, 33, 7145-7148. Bäeckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826-831.
4. For application of olefins flanking two stereogenic centers to a synthesis of natural products, see: Block, O.; Klein, G.; Altenbach, H.-J.; Brauer, D. J. J. Org. Chem. 2000, 65, 716-721. Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993-3005. Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655-12656. Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694-9696. Takeda, K.; Kaji, E.; Konda, Y.; Sato, N.; Nakamura, H.; Miya, N.; Morizane, A.; Yanagisawa, Y.; Akiyama, A.; Zen, S.; Harigaya, Y. Tetrahedron Lett. 1992, 33, 7145-7148. Bäeckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826-831.
5. For application of olefins flanking two stereogenic centers to a synthesis of natural products, see: Block, O.; Klein, G.; Altenbach, H.-J.; Brauer, D. J. J. Org. Chem. 2000, 65, 716-721. Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993-3005. Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655-12656. Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694-9696. Takeda, K.; Kaji, E.; Konda, Y.; Sato, N.; Nakamura, H.; Miya, N.; Morizane, A.; Yanagisawa, Y.; Akiyama, A.; Zen, S.; Harigaya, Y. Tetrahedron Lett. 1992, 33, 7145-7148. Bäeckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826-831.
6. For application of olefins flanking two stereogenic centers to a synthesis of natural products, see: Block, O.; Klein, G.; Altenbach, H.-J.; Brauer, D. J. J. Org. Chem. 2000, 65, 716-721. Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993-3005. Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655-12656. Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694-9696. Takeda, K.; Kaji, E.; Konda, Y.; Sato, N.; Nakamura, H.; Miya, N.; Morizane, A.; Yanagisawa, Y.; Akiyama, A.; Zen, S.; Harigaya, Y. Tetrahedron Lett. 1992, 33, 7145-7148. Bäeckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826-831.
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10. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
11. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
12. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
13. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
14. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
15. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
16. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
17. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
18. For selected recent reviews for Pd-catalyzed allylic substitutions, see: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943. Kazmaier, U. Curr. Org. Chem. 2003, 7, 317-328. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769. Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csöregh, I. Pure Appl. Chem. 1999, 71, 1477-1483. Poli, G.; Scolastico, C. Chemtracts 1999, 12, 822-836. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. Reiser, O. Angew. Chem. 1993, 105, 576-578. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. See also ref 2b.
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23. 1H NMR spectral data of a related compound. The assignment was confirmed by applying a modified Mosher method to anti-2. For data of the related compound, see: Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. For the modified Mosher method, see: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
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27. Absolute configuration of anti-8 was deduced by analogy to the reaction with benzylamine.
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34. Absolute configuration of anti-13 and anti-14 was determined by conversion into anti-6 and anti-7, respectively by deprotection of PMB ether followed by TBS protection.