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Volumn 11, Issue 19, 2000, Pages 3883-3886

Highly stereocontrolled reduction of 1,3-cyclopentanediones using oxazaborolidine -BH3

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE;

EID: 0034612959     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00378-5     Document Type: Article
Times cited : (31)

References (12)
  • 1
    • 0007436456 scopus 로고    scopus 로고
    • (a) Pankau, W. M.; Kreiser, W. Tetrahedron Lett. 1998, 39, 2089-2090. (b) Kreiser, W.; Wiggermann, A.; Kreif, A.; Swinnen, D. Tetrahedron Lett. 1996, 37, 7119-7122. (c) Breuilles, P.; Uguen, D. Tetrahedron Lett. 1988, 29, 201-204. (d) Corey, E. J.; Bakshi, R. K.; Shibata. S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. (e) Trost, B. M.; Shimizu, M. J. Am. Chem. Soc. 1983, 105, 6757-6759, and references cited therein.
  • 2
    • 0007379805 scopus 로고    scopus 로고
    • For reviews, see: (a) Singh, V. K. Synthesis 1992, 605-617. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784, and references cited therein.
  • 3
    • 0007459471 scopus 로고    scopus 로고
    • (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. (b) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477-511. (c) Harada, T.; Oku, A. Synlett 1994, 95-104, and the references cited therein.
  • 7
    • 0007410213 scopus 로고    scopus 로고
    • (a) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (b) Shimizu, M.; Tsukamoto, K.; Fujisawa, T. Tetrahedron Lett. 1997, 38, 5193-5196. (c) Shimizu, M.; Tsukamoto, K.; Matsutani, T.; Fujisawa, T. Tetrahedron 1998, 54, 10265-10274.
  • 8
    • 0007418893 scopus 로고    scopus 로고
    • 4 and appropriate functional group transformations. Cf. Brooks, D. W.; Mazdiyasni, H.; Grothaus, P. G. J. Org. Chem. 1987, 52, 3223-3232.
  • 9
    • 0007410214 scopus 로고    scopus 로고
    • 2 complex (0.1 mL, 1.0 mmol) in THF (3.0 mL) was added to the mixture over 3 h at 0°C. After stirring for 13 h at rt, the reaction mixture was quenched by adding 2N HCl, and the repeated extraction with ethyl acetate was followed by usual work-up which gave a crude oil that was purified on preparative TLC (eluent: n-Hex/AcOEt=2/1) to give the diol 3a as a colorless oil (33.0 mg, 80%).
  • 10
    • 0007429978 scopus 로고    scopus 로고
    • Absolute configurations of the products were determined by comparison with the authentic samples prepared via baker's yeast reduction of cyclopentan-1,2-diones. See Refs. 1a,b and 8.
  • 11
    • 0007426068 scopus 로고    scopus 로고
    • (a) Cai, D.; Tschaen, D.; Shi, Y. J.; Verhoeven, T. R.; Reamer, R. A.; Douglas, A. W. Tetrahedron Lett. 1993, 34, 3243-3246. (b) Shi, Y. J.; Cai, D.; Dolling, U. H.; Douglas, A. W.; Tschaen, D. M.; Verhoeven, T. R. Tetrahedron Lett. 1994, 35, 6409-6412. (c) Periosamy, M.; Kanth, J. V. B.; Prasad, A. S. B. Tetrahedron 1994, 50, 6411-6416. (d) Falorni, M.; Collu, C.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 2739-2742. (e) Saunkhe, A. M.; Burkhardt, E. R. Tetrahedron Lett. 1997, 38, 1523-1526. (f) Cho, B. T.; Chun. Y. S. J. Chem. Soc., Perkin Trans. 1 1999, 2095-2100.
  • 12
    • 0007379807 scopus 로고    scopus 로고
    • 3.THF complex (0.22 mL, 0.22 mmol) in THF (0.6 mL) was added to the mixture during 45 min at 0°C. After stirring for 19 h at rt, the reaction mixture was quenched by adding 2N HCl. Usual work-up followed by purification on preparative TLC (eluent: n-Hex/AcOEt=2/1) gave the β-hydroxy ketone 4a as a colorless oil (25.9 mg, 64%).


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