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Volumn 9, Issue 21, 2007, Pages 4367-4370

Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of α,β-unsaturated amides with ketones

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; AMIDE; COBALT; KETONE; UNCLASSIFIED DRUG;

EID: 35549009016     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701980e     Document Type: Article
Times cited : (42)

References (51)
  • 1
    • 0007180191 scopus 로고
    • For reviews of the Reformatsky reaction, see: For the reaction of zinc enolates with aldehydes and ketones, see: a
    • For the reaction of zinc enolates with aldehydes and ketones, see: (a) Reformatsky, S. Chem. Ber. 1887, 20, 1210-1211. For reviews of the Reformatsky reaction, see:
    • (1887) Chem. Ber , vol.20 , pp. 1210-1211
    • Reformatsky, S.1
  • 5
    • 33947443800 scopus 로고
    • For selected examples of the reaction of zinc enolatés with imines, see: a
    • For selected examples of the reaction of zinc enolatés with imines, see: (a) Gilman, H.; Speeter, M. J. Am. Chem. Soc. 1943, 65, 2255-2256.
    • (1943) J. Am. Chem. Soc , vol.65 , pp. 2255-2256
    • Gilman, H.1    Speeter, M.2
  • 8
    • 33646138279 scopus 로고    scopus 로고
    • For the use of zinc enolates in palladium-catalyzed α-arylations, see: a
    • For the use of zinc enolates in palladium-catalyzed α-arylations, see: (a) Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976-4985.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 4976-4985
    • Hama, T.1    Culkin, D.A.2    Hartwig, J.F.3
  • 11
    • 33845726636 scopus 로고    scopus 로고
    • For other recent methods of stoichiometric zinc enolate formation not discussed above, see: a
    • For other recent methods of stoichiometric zinc enolate formation not discussed above, see: (a) Dceda, Z.; Hirayama, T.; Matsubara, S. Angew. Chem., Int. Ed. 2006, 45, 8200-8203.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 8200-8203
    • Dceda, Z.1    Hirayama, T.2    Matsubara, S.3
  • 15
    • 3242668608 scopus 로고    scopus 로고
    • For selected examples of catalytic zinc enolate generation using substoichiometric quantities of chiral bimetallic zinc complexes, see: (a) Matsunaga, S, Yoshida, T, Morimoto, H, Kumagai, N, Shibasaki, M. J. Am. Chem. Soc 2004, 126, 8777-8785
    • For selected examples of catalytic zinc enolate generation using substoichiometric quantities of chiral bimetallic zinc complexes, see: (a) Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc 2004, 126, 8777-8785.
  • 23
    • 0030586106 scopus 로고    scopus 로고
    • For selected examples of sequential catalytic asymmetric conjugate addition-electrophilic trapping reactions using organozinc reagents, see: For an early report, see: a
    • For an early report, see: (a) Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141-5144. For selected examples of sequential catalytic asymmetric conjugate addition-electrophilic trapping reactions using organozinc reagents, see:
    • (1996) Tetrahedron Lett , vol.37 , pp. 5141-5144
    • Kitamura, M.1    Miki, T.2    Nakano, K.3    Noyori, R.4
  • 31
    • 24044546502 scopus 로고    scopus 로고
    • For recent examples of catalytic enantioselective conjugate additions of organozinc reagents to αβ-unsaturated carboxylic acid derivatives, see: (a) Brown, M. K, Degrado, S. J, Hoveyda, A. H. Angew. Chem, Int. Ed. 2005, 44, 5306-5310
    • For recent examples of catalytic enantioselective conjugate additions of organozinc reagents to αβ-unsaturated carboxylic acid derivatives, see: (a) Brown, M. K.; Degrado, S. J.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2005, 44, 5306-5310.
  • 35
    • 0001899091 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, 2005-2008.
    • (1989) Chem. Lett , pp. 2005-2008
    • Isayama, S.1    Mukaiyama, T.2
  • 36
    • 0037077589 scopus 로고    scopus 로고
    • For reductive aldol reactions catalyzed by other metals, see references cited within
    • (b) Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Lynch, V.; Schultz, A. J.; Wang, X.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448-9453. For reductive aldol reactions catalyzed by other metals, see references cited within:
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 9448-9453
    • Wang, L.-C.1    Jang, H.-Y.2    Roh, Y.3    Lynch, V.4    Schultz, A.J.5    Wang, X.6    Krische, M.J.7
  • 42
    • 4544221000 scopus 로고    scopus 로고
    • (h) Chiu, P. Synthesis 2004, 2210-2215.
    • (2004) Synthesis , pp. 2210-2215
    • Chiu, P.1
  • 44
    • 25444446131 scopus 로고    scopus 로고
    • For catalytic enantioselective reductive aldol reactions with ketones, see: a
    • For catalytic enantioselective reductive aldol reactions with ketones, see: (a) Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225-4228.
    • (2005) Org. Lett , vol.7 , pp. 4225-4228
    • Lam, H.W.1    Joensuu, P.M.2
  • 49
    • 35548931691 scopus 로고    scopus 로고
    • 2Zn, but with low diastereoselectivities. For example, methyl cinnamate reacts with acetophenone to produce a ca. 1:1 mixture of diastereomers.
    • 2Zn, but with low diastereoselectivities. For example, methyl cinnamate reacts with acetophenone to produce a ca. 1:1 mixture of diastereomers.
  • 50
    • 35548949503 scopus 로고    scopus 로고
    • The relative stereochemistry. of the known compound 5a was assigned by comparison with literature spectral data. The relative stereochemistries of 5c, 8f, and 8g were determined by X-ray crystallography. The stereochemistries of the remaining aldol products were assigned by analogy. See the Supporting Information for details.
    • The relative stereochemistry. of the known compound 5a was assigned by comparison with literature spectral data. The relative stereochemistries of 5c, 8f, and 8g were determined by X-ray crystallography. The stereochemistries of the remaining aldol products were assigned by analogy. See the Supporting Information for details.


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