메뉴 건너뛰기




Volumn 5, Issue 21, 2003, Pages 3875-3878

Intramolecular Cycloaddition Reactions of Silyl Nitronate Tethered to Vinylsilyl Group: 2-Nitroalkanols as Precursors for Amino Polyols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; HYDROXYL GROUP; NITRO DERIVATIVE; POLYOL; SILYL NITRONATE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0242712783     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035423v     Document Type: Article
Times cited : (25)

References (26)
  • 9
    • 0003527998 scopus 로고    scopus 로고
    • Wiley-VCH: New York
    • When 4-hydroxy-2-isoxazoline-2-oxides, prepared through base-promoted reaction of aldehydes bearing a leaving group on the α carbon with activated primary nitroalkanes, were treated with TMS-Cl (1 equiv) and imidazole at room temperature, heterotricyclic compounds were obtained as precursors for linear aminopolyhydroxylated structures; see ref 1c. Tandem inter [4 + 2]/intra [3 + 2] cycloaddition between siloxynitroalkene and chiral vinyl ether was successfully used for the synthesis of cyclic polyhydroxylated amine structures; see ref 1d. For a review, see: Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001; pp 263-274.
    • (2001) The Nitro Group in Organic Synthesis , pp. 263-274
    • Ono, N.1
  • 11
    • 0000851805 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, see also the review in ref 3, pp 30-65
    • (b) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 321-340; see also the review in ref 3, pp 30-65.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 321-340
    • Rosini, G.C.O.S.1
  • 14
    • 0013083033 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin
    • (c) For review, see: Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, pp 1075-1090.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1075-1090
    • Shibasaki, M.1    Gröger, H.2
  • 15
    • 0242510417 scopus 로고    scopus 로고
    • note
    • H-H values; see Supporting Information.
  • 16
    • 0002437012 scopus 로고    scopus 로고
    • Larson, G. L., Ed.; Jai Press: Greenwich
    • For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
    • (1996) Advances in Silicon Chemistry , vol.3 , pp. 1-62
    • Tamao, K.1
  • 17
    • 0030007621 scopus 로고    scopus 로고
    • For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
    • (1996) Tetrahedron , vol.57 , pp. 7599-7662
    • Jones, G.R.1    Landais, Y.2
  • 18
    • 0000276453 scopus 로고
    • For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
    • (1983) Organometallics , vol.2 , pp. 1694-1696
    • Tamao, K.1    Ishida, N.2    Tanaka, T.3    Kumada, M.4
  • 19
    • 0242678966 scopus 로고    scopus 로고
    • note
    • When chlorodiphenylvinylsilane was employed as a bis-silylating agent, a difficult to separate, multicomponent mixture was furnished as products.
  • 20
    • 0242595160 scopus 로고    scopus 로고
    • note
    • The relative configuration of minor diastereomer was assigned as 5 by careful analysis of NMR spectra.
  • 21
    • 0242678968 scopus 로고    scopus 로고
    • note
    • 1 substituent in the transition state.
  • 22
    • 84985092616 scopus 로고
    • One promising indirect way of observing the existence of such geometrical isomers of the silyl nitronate is to analyze the products distribution for an appropriate intermolecular cycloaddition reaction. We have not done it yet. Two possible mechanisms deserve consideration for such a geometrical isomerization of the nitronate: one involves a protonation- deprotonation process and the other involves the 1,3-migration of a trimethylsilyl group from one oxygen to another oxygen. For discussion with respect to the 1,3-migration, see: Colvin, E. W.; Beck, A. K.; Bastani, B.; Seebach, D.; Dunitz, J. D. Helv. Chim. Acta 1980, 63, 697-710.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 697-710
    • Colvin, E.W.1    Beck, A.K.2    Bastani, B.3    Seebach, D.4    Dunitz, J.D.5
  • 23
    • 0242510418 scopus 로고    scopus 로고
    • note
    • No effort has been made to optimize each step of these transformations. It turned out that similar reaction conditions as those employed for 4a or 4b were ineffective for cycloadduct 4c or 4e having a tertiary carbon linking to the nitrogen atom,. We are now making extensive efforts to establish the reaction conditions applicable to the transformation of 4c or 4e to amino polyol derivatives, which will be published elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.