Anti-selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing β-amino alcohols

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4712-4713

  Matsunaga, Shigeki ^a   Kumagai, Naoya ^a   Harada, Shinji ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

ALCOHOLS; AMINO ALCOHOLS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; IMINES; KETONES; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 0037462104     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034787f     Document Type: Article

References (26)

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2. For reviews on asymmetric synthesis of vicinalamino alcohols, see: (a) Bergmeire, S. C. Tetrahedron 2000, 56, 2561. (b) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; p 243.
3. For reviews on catalytic asymmetric Mannich-type Reaction, see: (a) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 954. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (c) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
4. For reviews on catalytic asymmetric Mannich-type Reaction, see: (a) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 954. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (c) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
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12. For other examples of direct catalytic asymmetric Mannich reaction using unmodified ketone and/or aldehyde as donors, see: (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (d) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
13. For other examples of direct catalytic asymmetric Mannich reaction using unmodified ketone and/or aldehyde as donors, see: (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (d) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
14. For other examples of direct catalytic asymmetric Mannich reaction using unmodified ketone and/or aldehyde as donors, see: (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (d) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
15. For other examples of direct catalytic asymmetric Mannich reaction using unmodified ketone and/or aldehyde as donors, see: (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (d) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
16. For other examples of direct catalytic asymmetric Mannich reaction using unmodified ketone and/or aldehyde as donors, see: (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. (c) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (d) Córdova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
17. For the synthesis of linked-BINOL 1, see: (a) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (b) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 4. Linked-BINOL is also commercially available from Wako Pure Chemical Industries, Ltd. Catalog No. for (S,S)-1: No. 152-02431.
18. For the synthesis of linked-BINOL 1, see: (a) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (b) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 4. Linked-BINOL is also commercially available from Wako Pure Chemical Industries, Ltd. Catalog No. for (S,S)-1: No. 152-02431.
19. (a) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
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24. Determined by NOE enhancement of cyclic carbamate synthesized from 4a.
25. The absolute configuration of 4b was determined by Mosher's method. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. The relative configuration of 4b was determined by X-ray analysis (see Figure 2).
26. Ramage, R.; Hopton, D.; Parrott, M. J. J. Chem. Soc., Perkin Trans. 1 1984, 1357.