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Volumn , Issue 9, 2004, Pages 1439-1445

Functionalized BINOL derivatives as ligands for enantioselectively catalyzed aldol additions: Highly enantioselective synthesis of chiral β-hydroxy thioesters

Author keywords

Aldol reaction; Binaphthalene; Bissteroidal ligand; Sonogashira reaction; Thioesters; Titanium

Indexed keywords

ALDEHYDES; DERIVATIVES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TITANIUM;

EID: 3042707283     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822364     Document Type: Article
Times cited : (15)

References (77)
  • 4
    • 0032512595 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357
    • Nelson, S.G.1
  • 5
    • 0001702357 scopus 로고    scopus 로고
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 998
    • Carreira, E.M.1
  • 6
    • 0034635481 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2000) Tetrahedron , vol.56 , pp. 917
    • Arya, P.1    Qin, H.2
  • 7
    • 0034678591 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1352
    • Machajewski, T.D.1    Wong, C.-H.2
  • 8
    • 4444360137 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2000) Angew. Chem. , vol.112 , pp. 1407
  • 9
    • 0037016618 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2002) Chem.-Eur. J. , vol.8 , pp. 36
    • Palomo, C.1    Oiarbide, M.2    Garcia, J.M.3
  • 10
    • 0037020389 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3554
    • Mikami, K.1    Terada, M.2    Matsuzawa, H.3
  • 11
    • 0012782728 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2002) Angew. Chem. , vol.114 , pp. 3704
  • 12
    • 1642386775 scopus 로고    scopus 로고
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 65
    • Palomo, C.1    Oiarbide, M.2    Garcia, J.M.3
  • 13
    • 0001524205 scopus 로고
    • Stereoselective Synthesis
    • 4th ed.; Thieme Verlag: Stuttgart
    • Reviews: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, Y., Eds.; Springer: Heidelberg, 1999, 998. (c) Arya, P.; Qin, H. Tetrahedron 2000, 56, 917. (d) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352; Angew. Chem. 2000, 112, 1407. (e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem.-Eur. J. 2002, 8, 36. (f) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem. Int. Ed. 2002, 41, 3554; Angew. Chem. 2002, 114, 3704. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (h) For the 'auxiliary-based' concept, see: Braun, M. Stereoselective Synthesis, In Houben-Weyl, Vol. E21/b, 4th ed.; Thieme Verlag: Stuttgart, 1995, 1603.
    • (1995) Houben-Weyl , vol.E21-B , pp. 1603
    • Braun, M.1
  • 14
    • 4243893500 scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 15
    • 33748238772 scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 417
    • Bach, T.1
  • 16
    • 0001134408 scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1994) Angew. Chem. , vol.106 , pp. 433
  • 17
    • 0029789545 scopus 로고    scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1262
    • Hoveyda, A.1    Morken, P.2
  • 18
    • 0001288714 scopus 로고    scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1996) Angew. Chem. , vol.108 , pp. 1378
  • 19
    • 0001604863 scopus 로고    scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1997) Gazz. Chim. Ital. , vol.127 , pp. 247
    • Cozzi, P.G.1    Tagliavini, E.2    Umani-Ronchi, A.3
  • 20
    • 33748844383 scopus 로고    scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (1997) J. Prakt. Chem. , vol.339 , pp. 758
    • Zimmer, R.1    Suhrbier, J.2
  • 21
    • 0042880939 scopus 로고    scopus 로고
    • Reviews: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417; Angew. Chem. 1994, 106, 433. (c) Hoveyda, A.; Morken, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; Angew. Chem. 1996, 108, 1378. (d) Cozzi, P. G.; Tagliavini, E.; Umani-Ronchi, A. Gazz. Chim. Ital. 1997, 127, 247. (e) Zimmer, R.; Suhrbier, J. J. Prakt. Chem. 1997, 339, 758. (f) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
    • (2003) Chem. Rev. , vol.103 , pp. 3155
    • Chen, Y.1    Yekta, S.2    Yudin, A.K.3
  • 32
    • 0001600602 scopus 로고    scopus 로고
    • Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3184; Angew. Chem. 1998, 110, 3369.
    • (1998) Angew. Chem. , vol.110 , pp. 3369
  • 37
    • 2342570203 scopus 로고    scopus 로고
    • (d) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566; Angew. Chem. 2004, 116, 1592.
    • (2004) Angew. Chem. , vol.116 , pp. 1592
  • 43
    • 0035907033 scopus 로고    scopus 로고
    • (b) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 1896; Angew. Chem. 2001, 113, 1949.
    • (2001) Angew. Chem. , vol.113 , pp. 1949
  • 51
    • 0344011477 scopus 로고    scopus 로고
    • (c) Yuan, Y.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2003, 42, 5478; Angew. Chem. 2003, 115, 5636.
    • (2003) Angew. Chem. , vol.115 , pp. 5636
  • 64
    • 3042744766 scopus 로고    scopus 로고
    • note
    • The NMR signals of the electronically deficient dibromo derivative (R)-6 are generally shifted upfield when compared with the unsubstituted (R)-4.


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