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Volumn 64, Issue 33, 2008, Pages 7729-7740

Racemic and asymmetric cobalt-catalysed reductive aldol couplings of α,β-unsaturated amides with ketones

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COBALT; DIETHYLZINC; KETONE DERIVATIVE; OXAZOLIDINE DERIVATIVE;

EID: 46149087013     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.022     Document Type: Article
Times cited : (27)

References (72)
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    • For a seminal reference, see:
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    • Revis, A.; Hilty, T.K. Tetrahedron Lett. 1987, 28, 4809-4812; For an extensive collection of reports of catalytic reductive aldol reactions, see references cited within:
    • Revis, A.; Hilty, T.K. Tetrahedron Lett. 1987, 28, 4809-4812; For an extensive collection of reports of catalytic reductive aldol reactions, see references cited within:
  • 3
    • 33846995439 scopus 로고    scopus 로고
    • Ngai, M.-Y.; Kong, J.-R.; Krische, M.J. J. Org. Chem. 2006, 72, 1063-1072; For relevant reviews, see:
    • Ngai, M.-Y.; Kong, J.-R.; Krische, M.J. J. Org. Chem. 2006, 72, 1063-1072; For relevant reviews, see:
  • 22
    • 46149101271 scopus 로고    scopus 로고
    • For cobalt-catalysed reductive aldol reactions, see:
    • For cobalt-catalysed reductive aldol reactions, see:
  • 27
    • 0026637875 scopus 로고
    • The relative stereochemistry of the known compound 4a was assigned by comparison with literature spectral data. See:
    • The relative stereochemistry of the known compound 4a was assigned by comparison with literature spectral data. See:. Taniguchi M., Hideaki F., Koichiro O., and Kiitiro U. Tetrahedron Lett. 33 (1992) 4353-4356
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4353-4356
    • Taniguchi, M.1    Hideaki, F.2    Koichiro, O.3    Kiitiro, U.4
  • 28
    • 46149117315 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for products 4c, 7f and 7g have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 666641-666643. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 29
    • 46149113286 scopus 로고    scopus 로고
    • note
    • For initial, speculative proposals about the mechanism of cobalt-catalysed conjugate reduction of α,β-unsaturated amides in the presence of diethylzinc, see Ref. 3a. Figure 1 presents a revised model.
  • 40
    • 0000487061 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon, Oxford
    • Heathcock C.H. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 181
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 181
    • Heathcock, C.H.1
  • 43
    • 46149098721 scopus 로고    scopus 로고
    • For chiral auxiliary-controlled asymmetric ketone aldol reactions, see:
    • For chiral auxiliary-controlled asymmetric ketone aldol reactions, see:
  • 53
    • 46149102741 scopus 로고    scopus 로고
    • For catalytic enantioselective aldol reactions of preformed enolates with ketones, see:
    • For catalytic enantioselective aldol reactions of preformed enolates with ketones, see:
  • 60
    • 33744923178 scopus 로고    scopus 로고
    • Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164-7165; For a catalytic enantioselective Reformatsky reaction with ketones, see:
    • Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164-7165; For a catalytic enantioselective Reformatsky reaction with ketones, see:
  • 62
    • 46149105257 scopus 로고    scopus 로고
    • note
    • For catalytic enantioselective reductive aldol reactions with ketones, see Refs.2b-e and 6a.
  • 63
    • 33847032528 scopus 로고    scopus 로고
    • For similar observations in related reactions, see Ref. 3a, and:
    • For similar observations in related reactions, see Ref. 3a, and:. Chrovian C.C., and Montgomery J. Org. Lett. 9 (2007) 537-540
    • (2007) Org. Lett. , vol.9 , pp. 537-540
    • Chrovian, C.C.1    Montgomery, J.2
  • 65
    • 0026657985 scopus 로고    scopus 로고
    • Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8645-8658; For the use of chiral oxazolidines in related reactions, see:
    • Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8645-8658; For the use of chiral oxazolidines in related reactions, see:
  • 68
    • 46149122781 scopus 로고    scopus 로고
    • note
    • The stereochemistries of the minor diastereomers produced in the reactions in Tables 4 and 5 were not determined.
  • 69
    • 46149101020 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for products 23a, 23d and 25f have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 634191-634193. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.