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Volumn 37, Issue 21, 2007, Pages 3751-3758

Samarium triiodide-catalyzed formation of Mannich-type products by amidoalkylation of 1,3-dicarbonyl compounds

Author keywords

1,3 dicarbonyl compounds; Amidoalkylation; Mannich type products; N (1 benzotriazol 1 ylalkyl)amides; SmI3

Indexed keywords

CARBONYL DERIVATIVE; IODINE DERIVATIVE; SAMARIUM; SAMARIUM TRIIODIDE; UNCLASSIFIED DRUG;

EID: 35348995956     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701569569     Document Type: Article
Times cited : (15)

References (16)
  • 1
    • 33747196381 scopus 로고    scopus 로고
    • Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B
    • (a) Hirose, T.; Sunazuka, T.; Yamamoto, D.; Kaji, E.; Ōmura, S. Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B. Tetrahedron Lett. 2006, 47 (58), 6761-6764;
    • (2006) Tetrahedron Lett , vol.47 , Issue.58 , pp. 6761-6764
    • Hirose, T.1    Sunazuka, T.2    Yamamoto, D.3    Kaji, E.4    Ōmura, S.5
  • 2
    • 0037028550 scopus 로고    scopus 로고
    • The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols
    • (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. J. Am. Chem. Soc. 2002, 124 (5), 827-833;
    • (2002) J. Am. Chem. Soc , vol.124 , Issue.5 , pp. 827-833
    • List, B.1    Pojarliev, P.2    Biller, W.T.3    Martin, H.J.4
  • 3
    • 2342521907 scopus 로고    scopus 로고
    • Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.
    • (c) Uraguchi, D.; Terada, M. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. J. Am. Chem. Soc. 2004, 126 (17), 5356-5357.
    • (2004) J. Am. Chem. Soc , vol.126 , Issue.17 , pp. 5356-5357
    • Uraguchi, D.1    Terada, M.2
  • 4
    • 23844490047 scopus 로고    scopus 로고
    • Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids
    • Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids. J. Am. Chem. Soc. 2005, 127 (32), 11256-11257.
    • (2005) J. Am. Chem. Soc , vol.127 , Issue.32 , pp. 11256-11257
    • Lou, S.1    Taoka, B.M.2    Ting, A.3    Schaus, S.E.4
  • 5
    • 33750463431 scopus 로고    scopus 로고
    • A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines
    • Bode, C. M.; Ting, A.; Schaus, S. E. A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines. Tetrahedron 2006, 62 (49), 11499-11505.
    • (2006) Tetrahedron , vol.62 , Issue.49 , pp. 11499-11505
    • Bode, C.M.1    Ting, A.2    Schaus, S.E.3
  • 6
    • 33646511310 scopus 로고    scopus 로고
    • The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids
    • Song, J.; Wang, Y.; Deng, L. The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: Enantioselective synthesis of β-amino acids. J. Am. Chem. Soc. 2006, 128 (18), 6048-6049.
    • (2006) J. Am. Chem. Soc , vol.128 , Issue.18 , pp. 6048-6049
    • Song, J.1    Wang, Y.2    Deng, L.3
  • 7
    • 30544448390 scopus 로고    scopus 로고
    • Phosphorodiamidic acid as a novel structural motif of Brønsted acid catalysts for direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds
    • Terada, M.; Sorimachi, K.; Uraguchi, D. Phosphorodiamidic acid as a novel structural motif of Brønsted acid catalysts for direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds. Synlett. 2006, 1, 133-136.
    • (2006) Synlett , vol.1 , pp. 133-136
    • Terada, M.1    Sorimachi, K.2    Uraguchi, D.3
  • 8
    • 33750366006 scopus 로고    scopus 로고
    • Enecarbamates as imine surrogates: Nucleophilic addition of 1,3-dicarbonyl compounds to enecarbamates
    • Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Enecarbamates as imine surrogates: nucleophilic addition of 1,3-dicarbonyl compounds to enecarbamates. Org. Lett. 2006, 8 (21), 4923-4925.
    • (2006) Org. Lett , vol.8 , Issue.21 , pp. 4923-4925
    • Kobayashi, S.1    Gustafsson, T.2    Shimizu, Y.3    Kiyohara, H.4    Matsubara, R.5
  • 9
    • 0001576828 scopus 로고
    • N-(1-Benzotriazol-1-ylalkyl) amides, versatile alpha-amidoalkylation reagents: Amidoalkylation of CH acids
    • Katritzky, A. R.; Pernak, J.; Fan,W. Q.; Saczewski, F. N-(1-Benzotriazol-1-ylalkyl) amides, versatile alpha-amidoalkylation reagents: Amidoalkylation of CH acids. J. Org. Chem. 1991, 56 (14), 4439-4443.
    • (1991) J. Org. Chem , vol.56 , Issue.14 , pp. 4439-4443
    • Katritzky, A.R.1    Pernak, J.2    Fan, W.Q.3    Saczewski, F.4
  • 10
    • 33646082005 scopus 로고    scopus 로고
    • Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
    • (a) Zou, X.; Wang, X.; Cheng, C.; Kong, L.; Mao, H. Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles. Tetrahedron Lett. 2006, 47 (22), 3767-3771;
    • (2006) Tetrahedron Lett , vol.47 , Issue.22 , pp. 3767-3771
    • Zou, X.1    Wang, X.2    Cheng, C.3    Kong, L.4    Mao, H.5
  • 11
    • 21544459927 scopus 로고    scopus 로고
    • Microwave-accelerated samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins
    • (b) Zhan, Z. P.; Lang, K. Microwave-accelerated samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins. Synlett. 2005, 10, 1551-1554.
    • (2005) Synlett , vol.10 , pp. 1551-1554
    • Zhan, Z.P.1    Lang, K.2
  • 12
    • 0037861871 scopus 로고    scopus 로고
    • Samarium(III) iodide complex catalyzed regioselective cleavage of epoxides to iodohydrins: Tandem epoxide opening-iodocyclization
    • (a) Kwon, D. W.; Cho, M. S.; Kim, Y. H. Samarium(III) iodide complex catalyzed regioselective cleavage of epoxides to iodohydrins: Tandem epoxide opening-iodocyclization. Synlett. 2003, 7, 959-946.
    • (2003) Synlett , vol.7 , pp. 959-946
    • Kwon, D.W.1    Cho, M.S.2    Kim, Y.H.3
  • 13
    • 0027208735 scopus 로고
    • Carbon-carbon double bond formation between α-haloketones and aldehydes promoted by samarium triiodide
    • Yu, Y.; Lin, R.; Zhang, Y. Carbon-carbon double bond formation between α-haloketones and aldehydes promoted by samarium triiodide. Tetrahedron Lett. 1993, 34 (28), 4547-4550.
    • (1993) Tetrahedron Lett , vol.34 , Issue.28 , pp. 4547-4550
    • Yu, Y.1    Lin, R.2    Zhang, Y.3
  • 14
    • 3042731170 scopus 로고    scopus 로고
    • Formation of α,α′-bis(substituted benzylidene)cycloalkanones from masked aldehydes promoted by samarium(III) triiodide
    • and the references cited therein
    • Wang, X.; Zhang, Y. Formation of α,α′-bis(substituted benzylidene)cycloalkanones from masked aldehydes promoted by samarium(III) triiodide. Chin. Chem. Lett. 2004, 15 (5), 511-514, and the references cited therein.
    • (2004) Chin. Chem. Lett , vol.15 , Issue.5 , pp. 511-514
    • Wang, X.1    Zhang, Y.2
  • 15
    • 0033215412 scopus 로고    scopus 로고
    • Preparation of β-amido ketones and aldehydes via amidoalkylation of eanmines, enol silyl ethers, and vinyl ethers
    • (a) Katritzky, A. R.; Fang, Y.; Silina, A. Preparation of β-amido ketones and aldehydes via amidoalkylation of eanmines, enol silyl ethers, and vinyl ethers. J. Org. Chem. 1999, 64 (20), 7622-7624;
    • (1999) J. Org. Chem , vol.64 , Issue.20 , pp. 7622-7624
    • Katritzky, A.R.1    Fang, Y.2    Silina, A.3
  • 16
    • 37049081144 scopus 로고
    • The chemistry of benzotriazoles, part 8: A novel two-step procedure for the N-alkylation of amides
    • (b) Barluenga, J.; Fernández-Simón, J. L.; Concellón, J. M.; Yus, M. The chemistry of benzotriazoles, part 8: A novel two-step procedure for the N-alkylation of amides. J. Chem. Soc., Perkin Trans. 1, 1988, 2339-2344.
    • (1988) J. Chem. Soc., Perkin Trans , vol.1 , pp. 2339-2344
    • Barluenga, J.1    Fernández-Simón, J.L.2    Concellón, J.M.3    Yus, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.