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Volumn 62, Issue 48, 2006, Pages 11090-11099

Stereoselective titanium-mediated aldol reactions of (S)-2-tert-butyldimethylsilyloxy-3-pentanone

Author keywords

Aldol reactions; Asymmetric reactions; Chiral ketone; Titanium enolates

Indexed keywords

2 TERT BUTYLDIMETHYLSILYLOXY 3 PENTANONE; ALDEHYDE; METHYL GROUP; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33749989298     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.034     Document Type: Article
Times cited : (26)

References (86)
  • 1
    • 0001524205 scopus 로고
    • Helmchen G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds), Thieme, Stuttgart
    • Braun M. In: Helmchen G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds). Methods of Organic Chemistry (Houben-Weyl). Stereoselective Synthesis Vol. E21b (1995), Thieme, Stuttgart 1603-1666
    • (1995) Methods of Organic Chemistry (Houben-Weyl). Stereoselective Synthesis , vol.E21b , pp. 1603-1666
    • Braun, M.1
  • 11
    • 33749989308 scopus 로고    scopus 로고
    • For aldol reactions based on lithium and titanium enolates from mandelic-derived ketone, see:
  • 17
    • 33750012331 scopus 로고    scopus 로고
    • For aldol reactions based on l-erythrulose-derived ketones, see:
  • 21
    • 0036775955 scopus 로고    scopus 로고
    • For lithium- and boron-mediated aldol reactions based on α-hydroxy ketones derived from 1,3-dioxan-4-yls, see:
    • For lithium- and boron-mediated aldol reactions based on α-hydroxy ketones derived from 1,3-dioxan-4-yls, see:. Hoffmann R.W., Mas G., and Brandl T. Eur. J. Org. Chem. (2002) 3455-3464
    • (2002) Eur. J. Org. Chem. , pp. 3455-3464
    • Hoffmann, R.W.1    Mas, G.2    Brandl, T.3
  • 22
    • 14844336872 scopus 로고    scopus 로고
    • For a recent review on the reactivity of dihydroxyacetone, see:
    • For a recent review on the reactivity of dihydroxyacetone, see:. Enders D., Voith M., and Lenzen A. Angew. Chem., Int. Ed. 44 (2005) 1304-1325
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1304-1325
    • Enders, D.1    Voith, M.2    Lenzen, A.3
  • 27
    • 0000444632 scopus 로고
    • Trost had already established the potentiality of lactate-derived methyl ketones in Mukaiyama aldol reactions:
    • Trost had already established the potentiality of lactate-derived methyl ketones in Mukaiyama aldol reactions:. Trost B.M., and Urabe H. J. Org. Chem. 55 (1990) 3982-3983
    • (1990) J. Org. Chem. , vol.55 , pp. 3982-3983
    • Trost, B.M.1    Urabe, H.2
  • 28
    • 33750006797 scopus 로고    scopus 로고
    • Liotta had also reported that lithium and sodium enolates from alanine-derived ketones produce highly stereoselective aldol processes, see:
  • 32
    • 31144452802 scopus 로고    scopus 로고
    • For a recent and comprehensive application of stereoselective aldol reactions based on ketones 3 and 4 to the synthesis of natural products, see:
    • For a recent and comprehensive application of stereoselective aldol reactions based on ketones 3 and 4 to the synthesis of natural products, see:. Crossman J.S., and Perkins M.V. J. Org. Chem. 71 (2006) 117-124
    • (2006) J. Org. Chem. , vol.71 , pp. 117-124
    • Crossman, J.S.1    Perkins, M.V.2
  • 37
    • 33749984204 scopus 로고    scopus 로고
    • For titanium-mediated aldol reactions based on chiral ketones, see:
  • 44
    • 33750000903 scopus 로고    scopus 로고
    • For boron-mediated aldol reactions based on lactate-derived chiral ketones, see:
  • 48
    • 33749992924 scopus 로고    scopus 로고
    • For applications to the synthesis of natural products, see:
  • 52
    • 33750005356 scopus 로고    scopus 로고
    • note
    • For preliminary communications, see: Refs. 16a and 18b.
  • 53
    • 0005878554 scopus 로고    scopus 로고
    • For a similar procedure, see:
    • For a similar procedure, see:. Denmark S.E., and Pham S.M. Org. Lett. 3 (2001) 2201-2204
    • (2001) Org. Lett. , vol.3 , pp. 2201-2204
    • Denmark, S.E.1    Pham, S.M.2
  • 54
    • 33750015009 scopus 로고    scopus 로고
    • note
    • 4-mediated aldol reaction involving isobutyraldehyde and benzaldehyde (1.2 equiv) for 10 min afforded 10a and 10e in 77% and 64% yield, respectively.
  • 55
    • 33750025657 scopus 로고    scopus 로고
    • note
    • 3, respectively.
  • 56
    • 0000584420 scopus 로고
    • Morrison J.D. (Ed), Academic, New York, NY Chapter 2
    • Heathcock C.H. In: Morrison J.D. (Ed). Asymmetric Synthesis Vol. 3 (1984), Academic, New York, NY 111-212 Chapter 2
    • (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
    • Heathcock, C.H.1
  • 57
    • 0035913767 scopus 로고    scopus 로고
    • For a recent discussion on aldol stereostructural assignments, see:
    • For a recent discussion on aldol stereostructural assignments, see:. Kitamura M., Nakano K., Miki T., Okada M., and Noyori R. J. Am. Chem. Soc. 123 (2001) 8939-8950
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8939-8950
    • Kitamura, M.1    Nakano, K.2    Miki, T.3    Okada, M.4    Noyori, R.5
  • 64
    • 33750011538 scopus 로고    scopus 로고
    • note
    • 2NEt/aldehyde 1:1.1:1.1:1.5) with longer enolization and reaction times (1.5 h and 1 h, respectively).
  • 71
    • 33750001989 scopus 로고    scopus 로고
    • For structural studies on six-coordinate titanium complexes, see:
  • 74
    • 33750028755 scopus 로고    scopus 로고
    • For a recent review on titanium complexes in enantioselective synthesis, see:
  • 79
    • 0001213599 scopus 로고    scopus 로고
    • For a review on models for 1,2-induction, see:
    • For a review on models for 1,2-induction, see:. Mengel A., and Reiser O. Chem. Rev. 99 (1999) 1191-1223
    • (1999) Chem. Rev. , vol.99 , pp. 1191-1223
    • Mengel, A.1    Reiser, O.2
  • 80
    • 33750025902 scopus 로고    scopus 로고
    • note
    • Adoption of the Felkin-anti-Felkin nomenclature does not imply any theoretical model.
  • 81
    • 33750032950 scopus 로고    scopus 로고
    • For recent studies on the stereochemical bias imparted by α-hydroxy aldehydes, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.