Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Synlett

Volumn , Issue 12, 2003, Pages 1865-1867

  Tamai, Tetsuo ^a   Asano, Shingo ^a   Totani, Kiichiro ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chiral auxiliary; D glucose; Nitrile oxides

Indexed keywords

GLUCOPYRANOSIDE; ISOXAZOLINE DERIVATIVE; METHYL 4 O ACRYLOYL 6 DEOXY O (TERT BUTYLDIMETHYLSILYL) ALPHA DEXTRO GLUCOPYRANOSIDE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLOADDITION; DIASTEREOISOMER; REDUCTION; STEREOCHEMISTRY;

EID: 0142060631     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41404     Document Type: Article

References (24)

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12. (a) For a recent review on [3+2] cycloadditions, see: Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
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16. 13C NMR, IR, and HRMS) in agreement with the structures depicted. Yields refer to purified sample by chromatography on silica gel.
17. 2 (96%). In benzene, the cycloaddition provided 3R in 92% yield, and the dr of the adducts was 99:1.
18. 3) was prepared: Curran, D. P.; Kim, B. H.; Daugherty, J.; Heffner, T. A. Tetrahedron Lett. 1988, 29, 3555.
19. 3) was prepared: Akiyama, T.; Okada, K.; Ozaki, S. Tetrahedron Lett. 1992, 33, 5766.
20. R (R) = 19.7 min (DAICEL Chiralcel OD-H, 2-propanol-hexane = 1:8).
21. R (R) = 25.2 min (DAICEL Chiralcel OJ-H, 2-propanol-hexane = 1:15).
22. Curran, D. P.; Kim, B. H.; Piyasena, H. P.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1987, 52, 2137.
23. The new template 9 was prepared from known compound 11 as shown below (Scheme 4). Compound 11 was prepared from tri-O-acetyl-D-glucal according to the reported procedure:Giuliano, R. M.; Jordan, A. D.; Gauthier, A. D.; Hoogsteen, K. J. Org. Chem. 1993, 58, 4979.
24. The dr of the cycloadduct 10 was precisely determined by the chiral HPLC analysis after converting the adduct into the isoxazoline derivative 7.