Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid: Application to catalytic asymmetric allylation of aldehydes

Journal of the American Chemical Society

Volumn 125, Issue 7, 2003, Pages 1708-1709

  Hanawa, Hideo ^a   Hashimoto, Takuya ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; LEWIS ACID; OXIDE; TITANIUM DERIVATIVE;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0037442960     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020338o     Document Type: Article

References (41)

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9. (b) Abe, N.; Hanawa, H.; Maruoka, K.; Sasaki, M.; Miyashita, M. Tetrahedron Lett. 1999, 40, 5369.
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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
24. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
25. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
26. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
27. 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) Keck, G. E.; Krishnamurthy, D.; Grier, N. C. J. Org. Chem. 1993, 58, 6543. (f) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323. (g) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (h) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (i) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077. (j) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (k) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J,; Shin, J. Chem. Commun. 1997, 761. (l) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889. (m) Marshall, J. A. Chemtracts 1997, 10, 649. (n) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (o) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357. (p) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935. (q) Hanawa, H.; Kii, S.; Maruoka, K. Adv. Synth. Catal. 2001, 343, 57. For another Ti-based coordination reagent, see: Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2768.
28. 3TiCl: Reetz, M. T.; Steinbach, R.; Kesseler, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 864.
29. Similar results were obtained by using the supernatant solution of the chiral bis-Ti(IV) oxide 1 after removal of the precipitated AgCl.
30. (a) Private communication from Professor K. B. Sharpless: Martin, C. A. Ph.D. Thesis, MIT 1988.
31. (b) Wang, J. T.; Fan, X.; Feng, X.; Qian, Y. M. Synthesis 1989, 291.
32. (c) Mikami, K. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995; Vol. 1, p 407.
33. ((S)-Binaphthoxy)isopropoxytitanium chloride: Seebach, D.: Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673.
34. 4], which is spectroscopically identical to that by the reported procedure (Sobota, P.; Przybylak, K.; Utko, J.; Jerzyhewicz, L. B.; Pombeiro, A. J. L.; Guedes da Silva, M. F. C.; Szczegot, K. Chem. Eur. J. 2001, 7, 951). See also: Terada, M.; Matsumoto, Y.: Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267.
35. 4], which is spectroscopically identical to that by the reported procedure (Sobota, P.; Przybylak, K.; Utko, J.; Jerzyhewicz, L. B.; Pombeiro, A. J. L.; Guedes da Silva, M. F. C.; Szczegot, K. Chem. Eur. J. 2001, 7, 951). See also: Terada, M.; Matsumoto, Y.: Nakamura, Y.; Mikami, K. Inorg. Chim. Acta 1999, 296, 267.
36. Some chiral BINOL-Ti(IV) complexes exist as dimeric species that exhibit chiral amplification phenomena. See ref 3g.
37. For details, see Supporting Information.
38. (a) Bradley, B. C.; Gaze, R.; Wardlaw, W. J. Chem. Soc. 1955, 721.
39. (b) Mukaiyama, T.; Inubushi. A.; Suda, S.; Hara, R.; Kobayashi, S. Chem. Lett. 1990, 1015.
40. (a) Terada, M.; Mikami. K. J. Chem. Soc., Chem. Commun. 1994, 833.
41. (b) Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861.