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Volumn 71, Issue 7, 2006, Pages 2888-2891

Thermal effects in the organocatalytic asymmetric Mannich reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; FORMALDEHYDE; IRRADIATION; KETONES; MICROWAVES; THERMAL EFFECTS;

EID: 33645507049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060064d     Document Type: Article
Times cited : (131)

References (37)
  • 2
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Chapter 26.2
    • (b) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, Chapter 26.2.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Denmark, S.E.1    Nicaise, O.J.-C.2
  • 13
    • 47749122232 scopus 로고    scopus 로고
    • Berkessel, A.. Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 5.2
    • (a) Asymmetric Organocatalysis; Berkessel, A.. Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 5.2.
    • (2005) Asymmetric Organocatalysis
  • 18
    • 33645520036 scopus 로고    scopus 로고
    • note
    • 4, and the resulting amino alcohols 5 (obtained as syn/anti mixtures, with the latter in excess) were then analyzed. For details, see Supporting Information.
  • 19
    • 11144325118 scopus 로고    scopus 로고
    • For recent reviews on the use of MWs in organic synthesis, see: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6250
    • Kappe, C.O.1
  • 22
    • 0141878086 scopus 로고    scopus 로고
    • Tierney, J. P., Lidström, P., Eds.; Blackwell: Oxford, U.K.
    • (d) Microwave Assisted Organic Synthesis; Tierney, J. P., Lidström, P., Eds.; Blackwell: Oxford, U.K., 2005.
    • (2005) Microwave Assisted Organic Synthesis
  • 23
    • 0011932271 scopus 로고    scopus 로고
    • Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany
    • (e) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
    • (2002) Microwaves in Organic Synthesis
  • 25
    • 0346456942 scopus 로고    scopus 로고
    • For a study describing the effect of MW in (nonasymmetric) Mannich-type reactions catalyzed by CuCl in conjunction with an ionic liquid, see: Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Diversity 2003, 7, 135.
    • (2003) Mol. Diversity , vol.7 , pp. 135
    • Leadbeater, N.E.1    Torenius, H.M.2    Tye, H.3
  • 29
    • 33645511507 scopus 로고    scopus 로고
    • note
    • Unfortunately, information on the reaction temperature of the experiments performed under MW irradiation is lacking in this article. Furthermore, a comparison with conventional methods of heating has not been reported.
  • 31
    • 23844498703 scopus 로고    scopus 로고
    • max = 40 °C) of the instrument. Thus, at the present stage, a reliable error margin of the given temperatures (Table 2) cannot be given. This should, however, not affect the reproducibility of the experiments. For a comparative study of temperature determinations under MW irradiations, see: Ondruschka, M. N. B.; Weiß, D.; Beckert, R.; Bonrath, W.; Gum, A. Chem. Eng. Technol. 2005, 28, 871.
    • (2005) Chem. Eng. Technol. , vol.28 , pp. 871
    • Ondruschka, M.N.B.1    Weiß, D.2    Beckert, R.3    Bonrath, W.4    Gum, A.5
  • 32
    • 33645508796 scopus 로고    scopus 로고
    • note
    • For comparison, the reaction between ketone 1a, formaldehyde (2a), and aniline (3a), catalyzed by 10 mol % of (S)-proline, was performed using MW irradiation without simultaneous cooling (15 W, 2.5 h; see also Table 2. entry 5). Under these conditions, the maximum temperature reached was 89 °C, and the product was obtained in just 53% yield, having an ee of 91%. (The temperature profile is included in Supporting Information).
  • 33
    • 33645507478 scopus 로고    scopus 로고
    • note
    • Reactions in oil bath were performed in the 10 mL glass vessels used in the MW-assisted experiments.
  • 34
    • 33645507125 scopus 로고    scopus 로고
    • Personal communication
    • Analogous observations have also been made in other organocatalytic Mannich-type reactions. Kappe, C. O.; Barbieri, V. Personal communication.
    • Kappe, C.O.1    Barbieri, V.2
  • 35
    • 0035813242 scopus 로고    scopus 로고
    • For an excellent discussion on MW effects in organic synthesis, see: Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
    • (2001) Tetrahedron , vol.57 , pp. 9199
    • Perreux, L.1    Loupy, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.