메뉴 건너뛰기




Volumn , Issue 22, 2010, Pages 3785-3801

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction

Author keywords

1,3 dicarbonyl compound; acid base combined salt catalyst; aldimine; asymmetric catalysis; direct Mannich type reaction

Indexed keywords

ACID-BASE COMBINED SALT CATALYST; ALDIMINE; ASYMMETRIC CATALYSIS; DICARBONYL COMPOUNDS; MANNICH-TYPE REACTIONS;

EID: 78149467804     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258296     Document Type: Review
Times cited : (73)

References (99)
  • 1
    • 1642415515 scopus 로고    scopus 로고
    • For reviews in direct Mannich-type reactions
    • For reviews in direct Mannich-type reactions, Córdova A, Acc. Chem. Res. 2004 37 102
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102
    • Córdova, A.1
  • 21
    • 0042880939 scopus 로고    scopus 로고
    • For reviews in BINOL chemistry
    • For reviews in BINOL chemistry, see:, Chen Y, Yekta S, Yudin A K., Chem. Rev. 2003 103 3155
    • (2003) Chem. Rev. , vol.103 , pp. 3155
    • Chen, Y.1    Yekta, S.2    Yudin, A.K.3
  • 26
    • 0001075233 scopus 로고
    • a value for 1,3-dicarbonyl compounds
    • a value for 1,3-dicarbonyl compounds, see:, Olmstead W N., Bordwell F G., J. Org. Chem. 1980 45 3299
    • (1980) J. Org. Chem. , vol.45 , pp. 3299
    • Olmstead, W.N.1    Bordwell, F.G.2
  • 29
    • 0034234818 scopus 로고    scopus 로고
    • Achiral diarylammonium arenesulfonates for ester condensation reactions
    • Achiral diarylammonium arenesulfonates for ester condensation reactions, see:, Wakasugi K, Misaki T, Yamada K, Tanabe Y, Tetrahedron Lett. 2000 41 5249
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5249
    • Wakasugi, K.1    Misaki, T.2    Yamada, K.3    Tanabe, Y.4
  • 33
    • 78149466331 scopus 로고    scopus 로고
    • Asymmetric catalysis by ammonium sulfonates, see: aza-Henry reactions
    • Asymmetric catalysis by ammonium sulfonates, see: aza-Henry reactions
  • 40
    • 52149105532 scopus 로고    scopus 로고
    • List and co-workers reported asymmetric catalysis with BINSA, where the enantioselectivities were 0-5% ee
    • List and co-workers reported asymmetric catalysis with BINSA, where the enantioselectivities were 0-5% ee:, Kampen D, Ladépe○che A, Claßen G, List B, Adv. Synth. Catal. 2008 350 962
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 962
    • Kampen, D.1    Ladépêche, A.2    Claßen, G.3    List, B.4
  • 42
    • 33751385897 scopus 로고
    • In the original literature, the Newman-Kwart rearrangement was examined at 285-400 C, see
    • In the original literature, the Newman-Kwart rearrangement was examined at 285-400 C, see:, Fabbri D, Delogu G, DeLucchi O, J. Org. Chem. 1993 58 1748
    • (1993) J. Org. Chem. , vol.58 , pp. 1748
    • Fabbri, D.1    Delogu, G.2    Delucchi, O.3
  • 44
    • 38949195951 scopus 로고    scopus 로고
    • A 1-400-kg-scale synthesis of aryl S -thiocarbamates from aryl O -thiocarbamates in microwave reactors was reported by Moseley and co-workers. The industrial synthesis of 6 should be a great advantage, see
    • A 1-400-kg-scale synthesis of aryl S -thiocarbamates from aryl O -thiocarbamates in microwave reactors was reported by Moseley and co-workers. The industrial synthesis of 6 should be a great advantage, see:, Moseley J D., Lenden P, Lockwood M, Ruda K, Sherlock J.-P, Thomson A D., Gilday J P., Org. Process Res. Dev. 2008 12 30
    • (2008) Org. Process Res. Dev. , vol.12 , pp. 30
    • Moseley, J.D.1    Lenden, P.2    Lockwood, M.3    Ruda, K.4    Sherlock, J.-P.5    Thomson, A.D.6    Gilday, J.P.7
  • 58
    • 0342302945 scopus 로고    scopus 로고
    • Chiral Li(I)-BINOLate catalyses
    • Chiral Li(I)-BINOLate catalyses, see:, Schiffers R, Kagan H B., Synlett 1997 1175
    • (1997) Synlett , pp. 1175
    • Schiffers, R.1    Kagan, H.B.2
  • 67
    • 0000768734 scopus 로고
    • Mg(II)-BINOLates have received little attention in asymmetric catalysis, see
    • Mg(II)-BINOLates have received little attention in asymmetric catalysis, see:, Noyori R, Suga S, Kawai K, Okada S, Kitamura M, Pure Appl. Chem. 1988 60 1597
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1597
    • Noyori, R.1    Suga, S.2    Kawai, K.3    Okada, S.4    Kitamura, M.5
  • 72
  • 78
    • 38349189109 scopus 로고    scopus 로고
    • For reviews on chiral phosphoric acid, see
    • For reviews on chiral phosphoric acid, see:, Akiyama T, Chem. Rev. 2007 107 5744
    • (2007) Chem. Rev. , vol.107 , pp. 5744
    • Akiyama, T.1
  • 84
    • 0001708390 scopus 로고
    • Selected pioneering reports of asymmetric catalyses using phosphoric acid-metal salts, see
    • Selected pioneering reports of asymmetric catalyses using phosphoric acid-metal salts, see:, Alper H, Hamel N, [nl]J. Am. Chem. Soc. 1990 112 2803
    • (1990) [Nl]J. Am. Chem. Soc. , vol.112 , pp. 2803
    • Alper, H.1    Hamel, N.2
  • 91
    • 77956019829 scopus 로고    scopus 로고
    • After our publication of ref. 24, List and co-workers reported their investigation of the metal impurities in phosphoric acid. A trace-element analysis by ICP-OES revealed that various alkali and alkaline earth metals were present as major impurities in the order Ca > Na > Mg > Si >> other metals. They warned that these impurities could impair the catalytic activities of the expected phosphoric acid, such as in asymmetric hydrogenation.
    • After our publication of ref. 24, List and co-workers reported their investigation of the metal impurities in phosphoric acid. A trace-element analysis by ICP-OES revealed that various alkali and alkaline earth metals were present as major impurities in the order Ca > Na > Mg > Si >> other metals. They warned that these impurities could impair the catalytic activities of the expected phosphoric acid, such as in asymmetric hydrogenation., Klussmann M, Ratjen L, Hoffmann S, Wakchaure V, Goddard R, List B, Synlett 2010 2189
    • (2010) Synlett , pp. 2189
    • Klussmann, M.1    Ratjen, L.2    Hoffmann, S.3    Wakchaure, V.4    Goddard, R.5    List, B.6
  • 92
    • 54049122287 scopus 로고    scopus 로고
    • Diastereoselective direct Mannich-type reaction of monothioesters, see
    • Diastereoselective direct Mannich-type reaction of monothioesters, see:, Utsumi N, Kitagaki S, Barbas C F. III, Org. Lett. 2008 10 3405
    • (2008) Org. Lett. , vol.10 , pp. 3405
    • Utsumi, N.1    Kitagaki, S.2    Barbas III, C.F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.