Novel cationic titanium(IV) Lewis acids and their use in asymmetric aldol reactions

Tetrahedron

Volumn 54, Issue 5-6, 1998, Pages 727-734

  Ishimaru, Kaori ^a,b   Monda, Keiji ^a   Yamamoto, Yohsuke ^a   Akiba, Kin Ya ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0032576833     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10296-4     Document Type: Article

References (33)

1. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
2. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
3. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
4. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
5. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
6. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
7. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
8. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
9. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
10. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
11. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
12. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
13. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
14. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
15. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
16. 2) Recent books, reviews and reports: Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Seyden-Penne, J. ed.; 1995, John Wiley & Sons, New York. Asymmetric Synthetic Methodology, Ager, D. J.; East, M. B. eds.; 1995, CRC Press, Boca Raton. Handbook of Enantioselective Catalysis, Vols. 1, 2 Brunner, H.; Zettlemeier, W. eds.; 1993, VCH, Weinheim. Catalytic Asymmetric Synthesis, Ojima, I. ed.; 1993, VCH, Weinheim. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. Hayashi, M.; Oguni, N. Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem., Jpn.) 1994, 52, 488. Soai, K.; Inoue, Y.; Takahashi, T.; Shibata, T. Tetrahedron 1996, 52, 13355. Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
17. 3) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Tomioka, K. Synthesis 1990, 541. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
18. 3) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Tomioka, K. Synthesis 1990, 541. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
19. 3) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Tomioka, K. Synthesis 1990, 541. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
20. 3) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Tomioka, K. Synthesis 1990, 541. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
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23. 5) Jones, V.; Frenking, G.; Reetz, M. F. Organometallics 1993, 12, 2111. Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561.
24. 6) Somewhat lower ee was observed when the reaction was carried out without molecular sieves 4A and 2,6-di-tert-butyl-4-methylpyridine.
25. 7) The cationic species could not be characterized because of their thermal instability and moisture sensitivity. However, quantitative formation of AgCl, which was characterized by powder X-ray analysis of a precipitate formed in the reaction of 7 (or 8) with silver hexafluoroantimonate, might suggest the generation of the cationic species. We are grateful to professor Koji Yamada and professor Tsutomu Okuda for measurement of powder X-ray diffraction.
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