Development of a chiral propionaldehyde homoenolate equivalent which reacts with imines with excellent stereoselectivity: Efficient and practical synthesis of optically active γ-amino carbonyl compounds [12]

Journal of the American Chemical Society

Volumn 121, Issue 50, 1999, Pages 11916-11917

  Teng, Xin ^a   Takayama, Yuuki ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBONYL DERIVATIVE; IMINE; PROPIONALDEHYDE; TITANIUM DERIVATIVE;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; LETTER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033596331     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9933487     Document Type: Letter

References (35)

1. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
2. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
3. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
4. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
5. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
6. Reviews: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
7. Review: Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.
8. Even in achiral form, to our best knowledge, only one precedent of homoenolate equivalents which react with imines (but not a propionaldehyde homoenolate equivalent) has been reported: Fang, J.-M.; Chen, S. T.; Chen, I.-H. J. Organomet. Chem. 1990, 398, 219.
9. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
10. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
11. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
12. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
13. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
14. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
15. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
16. For the asymmetric nucleophilic addition reactions to imines, see reviews: Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. Bloch, R. Chem. Rev. 1998, 98, 1407. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Kleinman, E. F.; Volkmann, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 893. Most recent examples: Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
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