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Volumn 47, Issue 45, 2008, Pages 8700-8702

Aminocatalytic enantioselective anti-mannich reaction of aldehydes with in situ generated N-cbz and N-boc imines

Author keywords

Aldehydes; Asymmetric catalysis; Imines; Mannich reaction; Organocatalysis

Indexed keywords

ALDEHYDES; AMINES; CATALYSIS; CHEMICAL REACTIONS; NITROGEN COMPOUNDS; REACTION KINETICS; SULFUR COMPOUNDS;

EID: 55249112288     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803819     Document Type: Article
Times cited : (98)

References (40)
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    • For recent reviews on asymmetric organocatalytic Mannich reactions, see: a
    • For recent reviews on asymmetric organocatalytic Mannich reactions, see: a) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797;
    • (2007) Eur. J. Org. Chem , pp. 5797
    • Ting, A.1    Schaus, S.E.2
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    • For reviews on asymmetric aminocatalysis, see: a
    • For reviews on asymmetric aminocatalysis, see: a) C. F. Barbas III, Angew. Chem. 2008, 120, 44;
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    • For an explanation of the origin of the anti selectivity observed in the direct asymmetric Mannich reaction catalyzed by 1, see: f I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760.
    • For an explanation of the origin of the anti selectivity observed in the direct asymmetric Mannich reaction catalyzed by 1, see: f) I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760.
  • 26
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    • For the first proline-catalyzed asymmetric Mannich reaction of a ketone and N-Boc imines (two examples), see: c) D. Enders, C. Grondal, M. Vrettou, Synthesis 2006, 3597.
    • For the first proline-catalyzed asymmetric Mannich reaction of a ketone and N-Boc imines (two examples), see: c) D. Enders, C. Grondal, M. Vrettou, Synthesis 2006, 3597.
  • 27
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    • For a comprehensive review on the usefulness of α-amido sulfones, see
    • For a comprehensive review on the usefulness of α-amido sulfones, see: M. Petrini, Chem. Rev . 2005, 105, 3949.
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  • 32
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    • N-carbamate-protected α-imino esters are known to be unstable, and their use in organic synthesis has been rather limited. Generally, they must be used immediately after their preparation; see, for example: a Y. Nakamura, R. Matsubara, H. Kiyohara, S. Kobayashi, Org. Lett. 2003, 5, 2481.
    • N-carbamate-protected α-imino esters are known to be unstable, and their use in organic synthesis has been rather limited. Generally, they must be used immediately after their preparation; see, for example: a) Y. Nakamura, R. Matsubara, H. Kiyohara, S. Kobayashi, Org. Lett. 2003, 5, 2481.
  • 33
    • 25844445144 scopus 로고    scopus 로고
    • For an asymmetric organocatalytic Mannich reaction of Boc-imino ester, generated in situ by following the procedure developed by Kobayashi, see: b
    • For an asymmetric organocatalytic Mannich reaction of Boc-imino ester, generated in situ by following the procedure developed by Kobayashi, see: b) T. B. Poulsen, C. Alemparte, S. Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956;
    • (2005) Angew. Chem , vol.117 , pp. 2956
    • Poulsen, T.B.1    Alemparte, C.2    Saaby, S.3    Bella, M.4    Jørgensen, K.A.5
  • 35
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    • 3, 24 h, 65 % yield, 84:16 d.r. and 85 % ee; compare with entry 2 in Table 1).
    • 3, 24 h, 65 % yield, 84:16 d.r. and 85 % ee; compare with entry 2 in Table 1).
  • 36
    • 55249122196 scopus 로고    scopus 로고
    • Aminocatalytic Mannich strategies are limited to N-Boc-protected imines; see Ref. [5]. Extension of our method to Fmoc-protected aminosulfone (Fmoc = 9-fluorenylmethyloxycarbonyl) failed under the reported reaction conditions.
    • Aminocatalytic Mannich strategies are limited to N-Boc-protected imines; see Ref. [5]. Extension of our method to Fmoc-protected aminosulfone (Fmoc = 9-fluorenylmethyloxycarbonyl) failed under the reported reaction conditions.
  • 40
    • 55249099181 scopus 로고    scopus 로고
    • Under the reported conditions, in situ generated cyclohexyl imine reacts very slowly, albeit with high stereocontrol (1 week, 12 % conversion, 95:5 d.r., 98 % ee). Studies are focusing on the identification of a more active catalytic system.
    • Under the reported conditions, in situ generated cyclohexyl imine reacts very slowly, albeit with high stereocontrol (1 week, 12 % conversion, 95:5 d.r., 98 % ee). Studies are focusing on the identification of a more active catalytic system.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.