Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 17, 1997, Pages 1871-1873

  Yamada, Yoichi M A ^a   Yoshikawa, Naoki ^a   Sasai, Hiroaki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldol reactions; Asymmetric catalysis; Asymmetric synthesis; Homogeneous catalysis; Lanthanum

Indexed keywords

EID: 0030863510     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199718711     Document Type: Article

References (13)

1. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
2. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
3. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
4. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
5. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
6. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
7. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
8. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
9. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
10. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
11. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
12. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.
13. For recent developments, see the following papers and the references cited therein: a) S. E. Denmark, S. B. D. Winter, X. Su, K.-T. Wong, J. Am. Chem. Soc. 1996, 118, 7404-7405; b) D. A. Evans, J. A. Murry, M. C. Kozlowski, ibid. 1996, 118, 5814-5815; c) R. A. Singer, E. M. Carreira, ibid. 1998, 117, 12360-12361; d) G. E. Keck, D. Krishnamurthy, ibid. 1995, 117, 2363-2364; e) M. Sodeoka, K. Ohrai, M. Shibasaki, J. Org. Chem. 1995, 60, 2648-2649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1994, 116, 4077-4078; g) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761-1772; h) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910; i) E. R. Parmee, Y. Hong, O. Tempkin, S. Masamune, ibid. 1992, 33, 1729-1732; j) S.Kiyooka,Y.Kaneko, K.Kume, ibid. 1992, 33, 4927-4930; k) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041-1042; 1) E. R. Parmee, O. Tempkin, S. Masamune, A. Abiko, ibid. 1991, 113, 9365-9366; m) K. Uotsu, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1995, 6, 71-74.