Catalytic asymmetric methallylation and propargylation of aldehydes with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1603-1605

  Konishi, Shunsuke ^a   Hanawa, Hideo ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; TITANIUM DIOXIDE; TRIBUTYLTIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 0037530087     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00247-7     Document Type: Article

References (42)

1. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
2. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
3. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
4. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
5. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
6. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
7. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley: New York, 1993, p. 1; (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 413; (c) Mikami, K. In Advance in Catalytic Process; Doyle, M. P., Ed.; JAI: Greenwich, 1995; p. 1; (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262; (e) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, p. 965; (f) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p. 299; (g) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, p. 403.
8. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
9. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
10. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
11. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
12. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
13. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
14. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
15. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
16. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
17. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
18. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
19. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
20. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
21. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
22. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
23. Allylation with BINOL/Ti(IV) complexes: (a) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783; (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; (d) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827; (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217; (f) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363; (g) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095; (h) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761; (i) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889; (j) Marshall, J. A. Chemtracts 1997, 10, 649; (k) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357; (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935; (m) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57; (n) Maruoka, K. Pure Appl. Chem. 2002, 74, 123; (o) Kii, S.; Maruoka, K. Chirality 2003, 15, 68. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
24. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
25. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
26. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
27. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
28. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
29. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
30. Catalytic asymmetric methallylation of aldehydes: (a) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543; (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077; (c) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289; (d) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189; (e) Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161; (f) Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88; (g) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140.
31. (a) Keck G.E., Krishnamurthy D., Chen X. Tetrahedron Lett. 35:1994;8323.
32. (b) Yu C.-M., Yoon S.-K., Choi H.-S., Baek K. Chem. Commun. 1997;763
33. Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392.
34. See also: Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Tino, R.; Umani-Ronchi, A. Tetrahedron: Asymmetry 2001, 12, 1063.
35. For example, catalytic asymmetric methallylation of cinnamaldehyde with BINOL-Ti(IV) complex at -20°C for 12 h gave 68% yield with 87% ee, while catalytic asymmetric methallylation of hydrocinnamaldehyde with BINAP-AgOTf complex at -20°C for 8 h afforded 22% yield with 70% ee. See Refs. 3a and 3f.
36. i is reported to accelerate such asymmetric propargylations (Refs. 4b,c).
37. Hanawa H., Hashimoto T., Maruoka K. J. Am. Chem. Soc. 125:2003;1708.
38. 3TiCl: Reetz M.T., Steinbach R., Kesseler K. Angew. Chem., Int. Ed. Engl. 21:1982;864.
39. Similar results were obtained by using the supernatant solution of the chiral bis-Ti(IV) oxide 1 after removal of the precipitated AgCl.
40. Private communication from Professor K. B. Sharpless: Martin, C. A. Ph.D. Thesis, MIT, 1988.
41. Wang J.T., Fan X., Feng X., Qian Y.M. Synthesis. 1989;291;
42. Mikami, K. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley, Chichester, 1995; Vol. 1, p. 407.