메뉴 건너뛰기




Volumn 41, Issue 4, 2008, Pages 95-104

Formation of C-C bonds via catalytic hydrogenation and transfer hydrogenation: Vinylation, allylation, and enolate addition

Author keywords

Aldol; Allylation; Allylic amines; Hydrogenation; Transfer hydrogenation

Indexed keywords


EID: 64849085420     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (70)

References (224)
  • 1
    • 0026418434 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Trost, B. M. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 8
    • 77549086868 scopus 로고    scopus 로고
    • Nobel Foundation, World Scientific Publishing: Singapore
    • Nobel Foundation. Nobel Lectures in Chemistry, 1901-1921; World Scientific Publishing: Singapore, 1999; pp 319-344.
    • (1999) Nobel Lectures in Chemistry, 1901-1921 , pp. 319-344
  • 15
    • 64849117596 scopus 로고    scopus 로고
    • Roelen, O. Chemische Verwertungsgesellschaft GmbH, Oberhausen, Ger. Patent DE 849,548, 1938; Chem. Abstr. 1944, 38, 5501.
    • Roelen, O. Chemische Verwertungsgesellschaft GmbH, Oberhausen, Ger. Patent DE 849,548, 1938; Chem. Abstr. 1944, 38, 5501.
  • 18
    • 0000193074 scopus 로고    scopus 로고
    • Prior to our systematic studies, only two isolated reports of hydrogenative C-C coupling had appeared in the literature: (a) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
    • Prior to our systematic studies, only two isolated reports of hydrogenative C-C coupling had appeared in the literature: (a) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
  • 20
    • 64849113136 scopus 로고    scopus 로고
    • On rare occasions, side products of reductive C-C-bond formation have been observed in catalytic hydrogenations: (a) Moyes, R. B.; Walker, D. W.; Wells, P. B.; Whan, D. A.; Irvine, E. A. In Catalysis and Surface Characterisation (Special Publication); Dines, T. J., Rochester, C. H., Thomson, J., Eds.; Royal Society of Chemistry, 1992; 114, pp 207-212.
    • On rare occasions, side products of reductive C-C-bond formation have been observed in catalytic hydrogenations: (a) Moyes, R. B.; Walker, D. W.; Wells, P. B.; Whan, D. A.; Irvine, E. A. In Catalysis and Surface Characterisation (Special Publication); Dines, T. J., Rochester, C. H., Thomson, J., Eds.; Royal Society of Chemistry, 1992; Vol. 114, pp 207-212.
  • 22
    • 38049063407 scopus 로고    scopus 로고
    • For recent reviews on hydrogen-mediated C-C couplings, see: a, Chiral Technologies Supplement
    • For recent reviews on hydrogen-mediated C-C couplings, see: (a) Ngai, M.-Y.; Krische, M. J. Chim. Oggi/Chemistry Today 2006, 24(4) (Chiral Technologies Supplement), 12.
    • (2006) Chim. Oggi/Chemistry Today , vol.24 , Issue.4 , pp. 12
    • Ngai, M.-Y.1    Krische, M.J.2
  • 23
    • 34347230462 scopus 로고    scopus 로고
    • Iida, H.; Krische, M. J. In Metal Catalyzed Reductive C-C Bond Formation; Krische, M. J., Ed.; Topics in Current Chemistry Series; Springer: Berlin, 2007; 279, pp 77-104.
    • (b) Iida, H.; Krische, M. J. In Metal Catalyzed Reductive C-C Bond Formation; Krische, M. J., Ed.; Topics in Current Chemistry Series; Springer: Berlin, 2007; Vol. 279, pp 77-104.
  • 28
    • 64849085333 scopus 로고    scopus 로고
    • For reviews encompassing the synthesis of allylic alcohols, see: a, 5th ed, Kroschwitz, J. 1, Ed, Wiley-Interscience: Hoboken, NJ
    • For reviews encompassing the synthesis of allylic alcohols, see: (a) Kirk-Othmer Encyclopedia of Chemical Technology, 5th ed.; Kroschwitz, J. 1., Ed.; Wiley-Interscience: Hoboken, NJ, 2004; Vol. 2, pp 234-249.
    • (2004) Kirk-Othmer Encyclopedia of Chemical Technology , vol.2 , pp. 234-249
  • 33
    • 0242646982 scopus 로고    scopus 로고
    • For reviews on the metal-catalyzed allylic amination and alkoxylation, see: a, Negishi, E, de Meijere, A, Eds, Wiley: New York
    • For reviews on the metal-catalyzed allylic amination and alkoxylation, see: (a) Acemoglu, L.; Williams, J. M. J. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley: New York, 2002; Vol. 2, pp 1689-1705.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 1689-1705
    • Acemoglu, L.1    Williams, J.M.J.2
  • 38
    • 84987584214 scopus 로고
    • For enantioselective catalytic additions of vinylzinc reagents to aldehydes, see: a
    • For enantioselective catalytic additions of vinylzinc reagents to aldehydes, see: (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 170
    • Oppolzer, W.1    Radinov, R.N.2
  • 56
    • 0037090420 scopus 로고    scopus 로고
    • For reviews encompassing catalytic enantioselective aldehyde vinylations using organozinc reagents, see: a
    • For reviews encompassing catalytic enantioselective aldehyde vinylations using organozinc reagents, see: (a) Wipf, P.; Kendall, C. Chem.-Eur. J. 2002, 8, 1778.
    • (2002) Chem.-Eur. J , vol.8 , pp. 1778
    • Wipf, P.1    Kendall, C.2
  • 58
    • 2542622015 scopus 로고    scopus 로고
    • For catalytic enantioselective ketone vinylation using organozinc reagents, see: a
    • For catalytic enantioselective ketone vinylation using organozinc reagents, see: (a) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 6538
    • Li, H.1    Walsh, P.J.2
  • 62
    • 0037467817 scopus 로고    scopus 로고
    • The catalyzed addition of vinylzirconocenes to imines is known, but enantioselective variants have not been developed: (a) Kakuuchi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 2003, 44, 923.
    • The catalyzed addition of vinylzirconocenes to imines is known, but enantioselective variants have not been developed: (a) Kakuuchi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 2003, 44, 923.
  • 64
    • 4544296892 scopus 로고    scopus 로고
    • The enantioselective Ni-catalyzed alkyne, imine, and tricthylborane three-component coupling has been reported, but modest selectivities (51-89% ee's) are observed. In this method, vinylation is accompanied by ethyl transfer: Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
    • The enantioselective Ni-catalyzed alkyne, imine, and tricthylborane three-component coupling has been reported, but modest selectivities (51-89% ee's) are observed. In this method, vinylation is accompanied by ethyl transfer: Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
  • 84
    • 33845568629 scopus 로고    scopus 로고
    • 5th ed, Kroschwitz, J. I, Ed, Wiley-Interscience: Hoboken, NJ
    • Kirk-Othmer Encyclopedia of Chemical Technology, 5th ed.; Kroschwitz, J. I., Ed.; Wiley-Interscience: Hoboken, NJ, 2004; Vol. 1, pp 216-217.
    • (2004) Kirk-Othmer Encyclopedia of Chemical Technology , vol.1 , pp. 216-217
  • 88
    • 0037000811 scopus 로고    scopus 로고
    • For reviews on enantioselective carbonyl allylations, see: a
    • For reviews on enantioselective carbonyl allylations, see: (a) Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
    • (2002) Aldrichimica Acta , vol.35 , pp. 23
    • Ramachandran, P.V.1
  • 94
    • 84980145665 scopus 로고    scopus 로고
    • Chirally modified allyl metal reagents: (a) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768.
    • Chirally modified allyl metal reagents: (a) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768.
  • 107
    • 85176698232 scopus 로고    scopus 로고
    • Catalytic asymmetric carbonyl allylation; (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem Soc. 1993, 115, 7001.
    • Catalytic asymmetric carbonyl allylation; (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem Soc. 1993, 115, 7001.
  • 111
    • 0000012889 scopus 로고    scopus 로고
    • For selected examples of reactions involving nucleophilic π-allyls, see: Palladium: (a) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195.
    • (37) For selected examples of reactions involving nucleophilic π-allyls, see: Palladium: (a) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195.
  • 119
    • 4544245462 scopus 로고    scopus 로고
    • For selected reviews covering carbonyl allylation via umpolung of π-allyls, see: a, Negishi, E, de Meijere, A, Eds, Wiley: New York
    • For selected reviews covering carbonyl allylation via umpolung of π-allyls, see: (a) Tamaru, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley: New York, 2002; Vol. 2, pp 1917-1943.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 1917-1943
    • Tamaru, Y.1
  • 124
    • 34250893845 scopus 로고    scopus 로고
    • The alcohol-unsaturate couplings developed in our laboratory provide products of carbonyl addition. To date, all other reported hydrogen auto-transfer processes provide products of oxidation-condensation-reduction, resulting in formal substitution of the alcohol. For recent reviews, see: a
    • The alcohol-unsaturate couplings developed in our laboratory provide products of carbonyl addition. To date, all other reported hydrogen auto-transfer processes provide products of oxidation-condensation-reduction, resulting in formal substitution of the alcohol. For recent reviews, see: (a) Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 2358
    • Guillena, G.1    Ramón, D.J.2    Yus, M.3
  • 128
    • 51649085840 scopus 로고    scopus 로고
    • Allenes also couple to carbonyl electrophiles under ruthenium-catalyzed transfer-hydrogenative conditions: Ngai, M.-Y; Skucas, E, Krische, M. J. Org. Lett. 2008, 10, 2705
    • (b) Allenes also couple to carbonyl electrophiles under ruthenium-catalyzed transfer-hydrogenative conditions: Ngai, M.-Y; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
  • 130
    • 0003627206 scopus 로고
    • The Chemistry of Ketenes, Allenes and Related Compounds
    • For reviews that encompass carbonyl propargylation employing allenyl metal reagents, see: a, Patai, S, Ed, Part, Wiley: New York
    • For reviews that encompass carbonyl propargylation employing allenyl metal reagents, see: (a) Moreau, J.-L. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Chemistry of Functional Groups Series, Part 1; Wiley: New York, 1980; pp 363-413.
    • (1980) Chemistry of Functional Groups Series , vol.1 , pp. 363-413
    • Moreau, J.-L.1
  • 133
    • 33744983663 scopus 로고    scopus 로고
    • Krause, N, Hashmi, A. S. K, Eds, Wiley-VCH: Weinheim
    • (d) Marshall, J. A.; Gung, B. W.; Grachan, M. L. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2005; Vol. 1, pp 493-592.
    • (2005) Modern Allene Chemistry , vol.1 , pp. 493-592
    • Marshall, J.A.1    Gung, B.W.2    Grachan, M.L.3
  • 135
    • 64849083442 scopus 로고    scopus 로고
    • For selected milestones in carbonyl propargylation, see: (a) Prévost, C.; Gaudemar, M.; Honigberg, J. C. R. Hebd. Seances Acad. Sci., Series IIc Chem. 1950,230, 1186.
    • For selected milestones in carbonyl propargylation, see: (a) Prévost, C.; Gaudemar, M.; Honigberg, J. C. R. Hebd. Seances Acad. Sci., Series IIc Chem. 1950,230, 1186.
  • 137
    • 64849094372 scopus 로고    scopus 로고
    • Karila, M.; Capmau, M. L.; Chodkiewicz, W. C. R. Hebd. Seances Acad. Sci., Series IIc Chem. 1969, 269, 342.
    • (c) Karila, M.; Capmau, M. L.; Chodkiewicz, W. C. R. Hebd. Seances Acad. Sci., Series IIc Chem. 1969, 269, 342.
  • 152
    • 64849110543 scopus 로고    scopus 로고
    • Though largely attributed to Wiirtz, the aldol reaction was reported first by Borodin: (a) Von Richter, V. Ber. Dtsch. Chem. Ges. 1869, 2, 552 Borodin's earliest results are cited in this article
    • Though largely attributed to Wiirtz, the aldol reaction was reported first by Borodin: (a) Von Richter, V. Ber. Dtsch. Chem. Ges. 1869, 2, 552 (Borodin's earliest results are cited in this article)
  • 155
  • 156
    • 0000244085 scopus 로고
    • For selected reviews on stereoselective aldol additions, see: a
    • For selected reviews on stereoselective aldol additions, see: (a) Heathcock, C. H. Science 1981, 214, 395.
    • (1981) Science , vol.214 , pp. 395
    • Heathcock, C.H.1
  • 157
    • 32644436285 scopus 로고
    • Asymmetric Reactions and Processes in Chemistry
    • Eliel, E. L, Otsuka, S, Eds, American Chemical Society: Washington, DC
    • (b) Heathcock, C. H. In Asymmetric Reactions and Processes in Chemistry; Eliel, E. L., Otsuka, S., Eds.; ACS Symposium Series 185; American Chemical Society: Washington, DC, 1982; pp 55-72.
    • (1982) ACS Symposium Series , vol.185 , pp. 55-72
    • Heathcock, C.H.1
  • 158
    • 0001924338 scopus 로고
    • Allinger, N. L, Eliel, E. L, Eds, Wiley: New York
    • (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-115.
    • (1982) Topics in Stereochemistry , vol.13 , pp. 1-115
    • Evans, D.A.1    Nelson, J.V.2    Taber, T.R.3
  • 161
    • 24044485355 scopus 로고    scopus 로고
    • For a recent review on the use of metallic catalysts for direct enantioselective aldol additions, see:, Mahrwald, R, Ed, Wiley-VCH: Weinheim
    • For a recent review on the use of metallic catalysts for direct enantioselective aldol additions, see: Shibasaki, M.; Matsunaga, S.; Kumagai, N. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 197-227.
    • (2004) Modern Aldol Reactions , vol.2 , pp. 197-227
    • Shibasaki, M.1    Matsunaga, S.2    Kumagai, N.3
  • 162
    • 13644256524 scopus 로고    scopus 로고
    • For recent reviews on the use of organic catalysts for direct enantioselective aldol additions, see: a, Mahrwald, R, Ed, Wiley-VCH: Weinheim
    • For recent reviews on the use of organic catalysts for direct enantioselective aldol additions, see: (a) List, B. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; Vol. 1, pp 161-200.
    • (2004) Modern Aldol Reactions , vol.1 , pp. 161-200
    • List, B.1
  • 164
    • 0034596299 scopus 로고    scopus 로고
    • A notable exception involves the direct asymmetric catalytic aldol additions to deliver glycolate aldol adducts. For examples, see: (a) Notz, W, List, B. J. Am. Chem. Soc. 2000,122,7386
    • A notable exception involves the direct asymmetric catalytic aldol additions to deliver glycolate aldol adducts. For examples, see: (a) Notz, W.; List, B. J. Am. Chem. Soc. 2000,122,7386.
  • 169
    • 34347225080 scopus 로고    scopus 로고
    • For recent reviews on the reductive aldol reaction, see: (a) Nishiyama, H.; Shiomi, T. In Metal Catalyzed Reductive C-C Bond Formation; Krische, M. J., Ed.; Topics in Current Chemistry Series; Springer: Berlin, 2007; 279, pp 105-137.
    • For recent reviews on the reductive aldol reaction, see: (a) Nishiyama, H.; Shiomi, T. In Metal Catalyzed Reductive C-C Bond Formation; Krische, M. J., Ed.; Topics in Current Chemistry Series; Springer: Berlin, 2007; Vol. 279, pp 105-137.
  • 170
    • 55549108533 scopus 로고    scopus 로고
    • Andersson, P. G, Munslow, I. J, Eds, Wiley-VCH: Weinheim
    • (b) Garner, S. A.; Krische, M. J. In Modern Reduction Methods; Andersson, P. G., Munslow, I. J., Eds.; Wiley-VCH: Weinheim, 2008; pp 387-408.
    • (2008) Modern Reduction Methods , pp. 387-408
    • Garner, S.A.1    Krische, M.J.2
  • 171
    • 0000191874 scopus 로고
    • For rhodium-catalyzed reductive aldol reactions mediated by silane, see: a
    • For rhodium-catalyzed reductive aldol reactions mediated by silane, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
    • (1987) Tetrahedron Lett , vol.28 , pp. 4809
    • Revis, A.1    Hilty, T.K.2
  • 184
    • 64849100062 scopus 로고    scopus 로고
    • For cobalt-catalyzed reductive aldol reactions, see: a
    • For cobalt-catalyzed reductive aldol reactions, see: (a) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 18, 2005.
    • (2005) Chem. Lett , vol.1989 , pp. 18
    • Isayama, S.1    Mukaiyama, T.2
  • 189
    • 0001494417 scopus 로고    scopus 로고
    • For iridium-catalyzed reductive aldol reactions, see
    • For iridium-catalyzed reductive aldol reactions, see Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
    • (2001) Org. Lett , vol.3 , pp. 1829
    • Zhao, C.-X.1    Duffey, M.O.2    Taylor, S.J.3    Morken, J.P.4
  • 190
    • 33751306191 scopus 로고    scopus 로고
    • For ruthenium-catalyzed reductive aldol reactions, see
    • For ruthenium-catalyzed reductive aldol reactions, see Doi, T.; Fukuyama, T.; Minamino, S.; Ryu, I. Synlett 2006, 3013.
    • (2006) Synlett , pp. 3013
    • Doi, T.1    Fukuyama, T.2    Minamino, S.3    Ryu, I.4
  • 191
    • 0032537679 scopus 로고    scopus 로고
    • For palladium-catalyzed reductive aldol reactions, see
    • For palladium-catalyzed reductive aldol reactions, see Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237.
    • (1998) Tetrahedron Lett , vol.39 , pp. 5237
    • Kiyooka, S.1    Shimizu, A.2    Torii, S.3
  • 192
    • 0032506682 scopus 로고    scopus 로고
    • For copper-promoted reductive aldol reactions, see: (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9229.
    • For copper-promoted reductive aldol reactions, see: (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9229.
  • 194
    • 64849086259 scopus 로고    scopus 로고
    • For copper-promoted reductive intramolecular Henry reaction, see Chung, W. K.; Chiu, P. Synlett 2005, 55.
    • (c) For copper-promoted reductive intramolecular Henry reaction, see Chung, W. K.; Chiu, P. Synlett 2005, 55.
  • 195
    • 9144228846 scopus 로고    scopus 로고
    • For copper-promoted and catalyzed reductive cyclizations of αβ-acetylenic ketones tethered to ketones, see Chiu, P, Leung, S. K. Chem. Commun. 2004, 2308
    • (d) For copper-promoted and catalyzed reductive cyclizations of αβ-acetylenic ketones tethered to ketones, see Chiu, P.; Leung, S. K. Chem. Commun. 2004, 2308.
  • 196
    • 0033548542 scopus 로고    scopus 로고
    • For copper-catalyzed reductive aldol reactions, see: (a) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133.
    • For copper-catalyzed reductive aldol reactions, see: (a) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133.
  • 204
    • 33847032528 scopus 로고    scopus 로고
    • For nickel-catalyzed reductive aldol reactions, see
    • For nickel-catalyzed reductive aldol reactions, see Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537.
    • (2007) Org. Lett , vol.9 , pp. 537
    • Chrovian, C.C.1    Montgomery, J.2
  • 205
    • 0013245322 scopus 로고    scopus 로고
    • For a reductive aldol coupling employing stoichiometric quantities of indium reagent, see
    • For a reductive aldol coupling employing stoichiometric quantities of indium reagent, see Inoue, K.; Ishida, T.; Shibata, I.; Baba, A. Adv. Synth. Catal. 2002, 344, 283.
    • (2002) Adv. Synth. Catal , vol.344 , pp. 283
    • Inoue, K.1    Ishida, T.2    Shibata, I.3    Baba, A.4
  • 208
    • 0037176242 scopus 로고    scopus 로고
    • For rhodium-catalyzed reductive aldol reactions mediated by hydrogen, see: a
    • For rhodium-catalyzed reductive aldol reactions mediated by hydrogen, see: (a) Jang, H.-Y; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 15156
    • Jang, H.-Y.1    Huddleston, R.R.2    Krische, M.J.3
  • 217
    • 0000131734 scopus 로고
    • For tri(2-furyl)phosphine and triphenylarsine effects in metal-catalyzed reactions, see: a
    • For tri(2-furyl)phosphine and triphenylarsine effects in metal-catalyzed reactions, see: (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991,113, 9585.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 9585
    • Farina, V.1    Krishnan, B.2
  • 221
    • 0036260038 scopus 로고    scopus 로고
    • For metal-catalyzed reductive Mannich couplings mediated by silane, see: a
    • For metal-catalyzed reductive Mannich couplings mediated by silane, see: (a) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284.
    • (2002) Chem. Commun , pp. 1284
    • Muraoka, T.1    Kamiya, S.2    Matsuda, I.3    Itoh, K.4
  • 223
    • 33748434728 scopus 로고    scopus 로고
    • For secondary-amine-catalyzed reductive Mannich coupling of enal to imines mediated by Hantzsch ester, see Zhao, G.-L, Cordova, A. Tetrahedron Lett. 2006, 47, 7417
    • For secondary-amine-catalyzed reductive Mannich coupling of enal to imines mediated by Hantzsch ester, see Zhao, G.-L.; Cordova, A. Tetrahedron Lett. 2006, 47, 7417.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.