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Volumn 48, Issue 18, 2009, Pages 3353-3356

Direct anti-selective catalytic asymmetric mannich-type reactions of α-ketoanilides for the synthesis of γ-amino amides and azetidine- 2-amides

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINES; BIPHENYLDIAMINE; BUILDING BLOCKES; CARBONYL COMPOUNDS; MANNICH-TYPE REACTIONS; NICKEL COMPLEX; SCHIFF-BASE;

EID: 70349784874     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900670     Document Type: Article
Times cited : (79)

References (62)
  • 1
    • 33846906752 scopus 로고    scopus 로고
    • For a recent general review on asymmetric Mannich(-type) reactions, see: G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541.
    • For a recent general review on asymmetric Mannich(-type) reactions, see: G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541.
  • 2
    • 70349928142 scopus 로고    scopus 로고
    • For recent reviews on direct catalytic asymmetric Mannich(-type) reactions to give ß-amino carbonyl compounds, see
    • For recent reviews on direct catalytic asymmetric Mannich(-type) reactions to give ß-amino carbonyl compounds, see:
  • 3
    • 70349954296 scopus 로고    scopus 로고
    • M. M. B. Marques, Angew. Chem. 2006, 118, 356; Angew. Chem. Int. Ed. 2006, 45, 348;
    • a) M. M. B. Marques, Angew. Chem. 2006, 118, 356; Angew. Chem. Int. Ed. 2006, 45, 348;
  • 9
    • 67749124296 scopus 로고    scopus 로고
    • for related studies on stereoselective homoenolate additions catalyzed by N-hetero-cyclic carbenes, see the following review
    • b) M. Rommel, T. Fukuzumi, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 17266; for related studies on stereoselective homoenolate additions catalyzed by N-hetero-cyclic carbenes, see the following review:
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 17266
    • Rommel, M.1    Fukuzumi, T.2    Bode, J.W.3
  • 11
    • 70349928164 scopus 로고    scopus 로고
    • K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. 2001, 40, 2995.
    • K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. 2001, 40, 2995.
  • 12
    • 70349951669 scopus 로고    scopus 로고
    • G. Lu, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 6953; Angew. Chem. Int. Ed. 2008, 47, 6847.
    • G. Lu, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 6953; Angew. Chem. Int. Ed. 2008, 47, 6847.
  • 13
    • 70349950096 scopus 로고    scopus 로고
    • For selected examples of other catalytic asymmetric approaches to the synthesis of γ-amino acids, see the following review on the synthesis of glutamic acid derivatives
    • For selected examples of other catalytic asymmetric approaches to the synthesis of γ-amino acids, see the following review on the synthesis of glutamic acid derivatives:
  • 14
    • 0036224968 scopus 로고    scopus 로고
    • for γ amination, see
    • a) V. A. Soloshonok, Curr. Org. Chem. 2002, 6, 341; for γ amination, see:
    • (2002) Curr. Org. Chem , vol.6 , pp. 341
    • Soloshonok, V.A.1
  • 15
    • 33749527371 scopus 로고    scopus 로고
    • S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973; see also the following review on the use of glycine Schiff bases as donors in asymmetric synthesis:
    • b) S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973; see also the following review on the use of glycine Schiff bases as donors in asymmetric synthesis:
  • 16
    • 70349953548 scopus 로고    scopus 로고
    • T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300; Angew. Chem. Int. Ed. 2007, 46, 4222.
    • c) T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300; Angew. Chem. Int. Ed. 2007, 46, 4222.
  • 17
    • 70349928162 scopus 로고    scopus 로고
    • For the use of related glyoxanilides as electrophiles in catalytic enantioselective reactions, see
    • For the use of related glyoxanilides as electrophiles in catalytic enantioselective reactions, see:
  • 19
    • 34547725857 scopus 로고    scopus 로고
    • for transformations of anilides into carboxylic acids, esters, amides, and alcohols under mild reaction conditions, see
    • b) D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2007, 129, 9606; for transformations of anilides into carboxylic acids, esters, amides, and alcohols under mild reaction conditions, see:
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 9606
    • Evans, D.A.1    Aye, Y.2
  • 23
    • 48249148123 scopus 로고    scopus 로고
    • For a recent review on bifunctional Lewis acid/Brønsted base asymmetric metal catalysis, see: S. Matsunaga, M. Shibasaki, Bull. Chem. Soc. Ipn. 2008, 81, 60.
    • For a recent review on bifunctional Lewis acid/Brønsted base asymmetric metal catalysis, see: S. Matsunaga, M. Shibasaki, Bull. Chem. Soc. Ipn. 2008, 81, 60.
  • 24
    • 70349975249 scopus 로고    scopus 로고
    • For a lanthanum/lithium catalyst, see
    • For a lanthanum/lithium catalyst, see:
  • 27
    • 70349937427 scopus 로고    scopus 로고
    • T. Yoshida, H. Morimoto, N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 3536; Angew. Chem. Int. Ed. 2005, 44, 3470; for an indium catalyst, see:
    • c) T. Yoshida, H. Morimoto, N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 3536; Angew. Chem. Int. Ed. 2005, 44, 3470; for an indium catalyst, see:
  • 28
    • 70349956007 scopus 로고    scopus 로고
    • S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439; Angew. Chem. Int. Ed. 2005, 44, 4365; for a barium catalyst, see:
    • d) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439; Angew. Chem. Int. Ed. 2005, 44, 4365; for a barium catalyst, see:
  • 32
    • 70349961049 scopus 로고    scopus 로고
    • For bifunctional dinuclear Schiff base catalysts developed by our research group, see: CuSm-la
    • For bifunctional dinuclear Schiff base catalysts developed by our research group, see: CuSm-la:
  • 34
    • 70349963973 scopus 로고    scopus 로고
    • 2-lb:
    • 2-lb:
  • 36
    • 70349939049 scopus 로고    scopus 로고
    • Z. Chen, M. Furutachi, Y. Kato, S. Matsunaga, M. Shibasaki, Angew. Chem. 2009, 121, 2252-2254; Angew. Chem. Int. Ed. 2009, 48, 2218-2220.
    • d) Z. Chen, M. Furutachi, Y. Kato, S. Matsunaga, M. Shibasaki, Angew. Chem. 2009, 121, 2252-2254; Angew. Chem. Int. Ed. 2009, 48, 2218-2220.
  • 37
    • 70349957559 scopus 로고    scopus 로고
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see:
  • 42
    • 67749143917 scopus 로고    scopus 로고
    • 2-Schiff base complexes as epoxidation catalysts, see also:
    • 2-Schiff base complexes as epoxidation catalysts, see also:
  • 44
    • 70349950088 scopus 로고    scopus 로고
    • For selected recent examples of the use of sulfonyl imines to improve stereoselectivity in asymmetric Mannich-type reactions, see
    • For selected recent examples of the use of sulfonyl imines to improve stereoselectivity in asymmetric Mannich-type reactions, see:
  • 45
    • 57149107381 scopus 로고    scopus 로고
    • J. Hernandez-Toribio, R. Gómez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2008, 130,16150, and references cited therein;
    • a) J. Hernandez-Toribio, R. Gómez Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2008, 130,16150, and references cited therein;
  • 47
    • 70349975241 scopus 로고    scopus 로고
    • For a review on the use of the Ns group in organic synthesis, see
    • For a review on the use of the Ns group in organic synthesis, see:
  • 48
    • 1442349810 scopus 로고    scopus 로고
    • 353; Ns-substituted imines 3 were synthesized by a literature procedure
    • a) T. Kan, T. Fukuyama, Chem. Commun. 2004, 353; Ns-substituted imines 3 were synthesized by a literature procedure:
    • (2004) Chem. Commun
    • Kan, T.1    Fukuyama, T.2
  • 53
    • 70349967244 scopus 로고    scopus 로고
    • For the stereoselective synthesis of azetidine-2-carboxylic acids (L-aze analogues) and their incorporation into peptides, see the following review:
    • For the stereoselective synthesis of azetidine-2-carboxylic acids (L-aze analogues) and their incorporation into peptides, see the following review:
  • 54
    • 4444226240 scopus 로고    scopus 로고
    • and references cited therein; for selected examples, see
    • a) F. Couty, G. Evano, D. Prim, Mini-Rev. Org. Chem. 2004, 1, 133, and references cited therein; for selected examples, see:
    • (2004) Mini-Rev. Org. Chem , vol.1 , pp. 133
    • Couty, F.1    Evano, G.2    Prim, D.3
  • 55
    • 29744444160 scopus 로고    scopus 로고
    • and references cited therein;
    • b) D. Enders, J. Gries, Synthesis 2005, 3508, and references cited therein;
    • (2005) Synthesis , pp. 3508
    • Enders, D.1    Gries, J.2
  • 58
    • 16044373080 scopus 로고    scopus 로고
    • A. P. Kozikowski, Y. Liao, W. Tückmantel, S. Wang, S. Pshenichkin, A. Surin, C. Thomsen, J. T. Wroblewski, Bioorg. Med. Chem. Lett. 1996, 6, 2559; for related studies, see also:
    • e) A. P. Kozikowski, Y. Liao, W. Tückmantel, S. Wang, S. Pshenichkin, A. Surin, C. Thomsen, J. T. Wroblewski, Bioorg. Med. Chem. Lett. 1996, 6, 2559; for related studies, see also:
  • 60
    • 70349954297 scopus 로고    scopus 로고
    • H. Morimoto, T. Yoshino, T. Yukawa, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 9265; Angew. Chem. Int. Ed. 2008, 47, 9125; for related studies on the synthesis of azetidines with the syn-syn and the anti-syn configuration, see also:
    • (a) H. Morimoto, T. Yoshino, T. Yukawa, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 9265; Angew. Chem. Int. Ed. 2008, 47, 9125; for related studies on the synthesis of azetidines with the syn-syn and the anti-syn configuration, see also:
  • 61
    • 70349937414 scopus 로고    scopus 로고
    • H. Morimoto, S. H. Wiedemann, A. Yamaguchi, S. Harada, Z. Chen, S. Matsunaga, M. Shibasaki, Angew. Chem. 2006, 118, 3218; Angew. Chem. Int. Ed. 2006, 45, 3146.
    • b) H. Morimoto, S. H. Wiedemann, A. Yamaguchi, S. Harada, Z. Chen, S. Matsunaga, M. Shibasaki, Angew. Chem. 2006, 118, 3218; Angew. Chem. Int. Ed. 2006, 45, 3146.
  • 62
    • 70349950075 scopus 로고    scopus 로고
    • At the moment, the reason for the high anti selectivity is not clear. We speculate that the cooperative function of two Ni centers may be important, as observed in our previous studies on different reactions with bimetallic Schiff base complexes.[10] Mechanistic studies to clarify the role in the present reaction of the two nickel atoms in the catalyst are ongoing
    • [10] Mechanistic studies to clarify the role in the present reaction of the two nickel atoms in the catalyst are ongoing.


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