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Volumn 71, Issue 4, 2006, Pages 1537-1544

Boron trifluoride-induced, new stereospecific rearrangements of chiral epoxy ethers. Ready access to enantiopure 4-(diarylmethyl)-1,3-dioxolanes and 4,5-disubstituted tetrahydrobenzo[c]oxepin-4-ols

Author keywords

[No Author keywords available]

Indexed keywords

ARYLGLYCIDOLS; BENZYL-TYPE ETHERS; FRIEDEL-CRAFTS TYPE;

EID: 33644554790     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052208e     Document Type: Article
Times cited : (28)

References (58)
  • 2
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    • Challener, C. A., Ed.; Ashgate: Burlington, VT
    • (b) Chiral Drugs; Challener, C. A., Ed.; Ashgate: Burlington, VT, 2001; p 278.
    • (2001) Chiral Drugs , pp. 278
  • 3
    • 0034596803 scopus 로고    scopus 로고
    • For recent work on preparation of enantiopure, heterosubstituted diarylmethanes by enantioselective phenyl transfer to aldehydes, see: (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem., Int. Ed. 2000, 39, 3465-3467.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3465-3467
    • Bolm, C.1    Hermanns, N.2    Hildebrand, J.P.3    Muniz, K.4
  • 12
    • 11444266045 scopus 로고    scopus 로고
    • For recent reviews on the chemistry of epoxides. see: (a) Pastor, I. M.; Yus, M. Curr. Org. Chem. 2005, 9, 1-29.
    • (2005) Curr. Org. Chem. , vol.9 , pp. 1-29
    • Pastor, I.M.1    Yus, M.2
  • 35
    • 0343126816 scopus 로고
    • For examples of 1,3-dioxolanes with nonequivalent, yet noncoupled C-2 protons, see: (a) Gras, J. L.; Poncet, A. Bull. Soc. Chim. Fr. 1991, 128, 566.
    • (1991) Bull. Soc. Chim. Fr. , vol.128 , pp. 566
    • Gras, J.L.1    Poncet, A.2
  • 38
    • 33644545227 scopus 로고    scopus 로고
    • note
    • 2 at room temperature for 3 h. The reaction mixture was filtered through a short pad of Celite, the solvent was evaporated in vacuo, and the resulting oil (0.011 g) was used for the next reaction without purification.
  • 39
    • 33644505972 scopus 로고    scopus 로고
    • note
    • 3) δ 2.45 (s, 6H), 3.54 (dd, J = 6.8, 8.4 Hz, 1H), 3.84 (dd, J = 6.4, 8.4 Hz, 1H), 4.04 (d, J = 9.2 Hz, 1H), 4.70 (m, 1H), 4.96 (s, 1H), 5.06 (s, 1H), 6.96 (d, J = 8.4 Hz, 4H), 7.20-7.32 (m, 8H), 7.78 (d, J = 8.4 Hz, 5H)]. A recrystallization from dichloromethane afforded crystals suitable for X-ray diffraction.
  • 45
    • 3543079935 scopus 로고    scopus 로고
    • For a recent account on the rearrangement of silyl ethers of glycidols to β-alkoxyaldehydes catalyzed by a Cr(III) porphyrin complex, see: Suda, K.; Kikkawa, T.; Nakajima, S.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554-9555.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9554-9555
    • Suda, K.1    Kikkawa, T.2    Nakajima, S.3    Takanami, T.4
  • 50
    • 33644538405 scopus 로고    scopus 로고
    • note
    • A Friedel-Crafts type mechanism was discarded for this process on the basis of the inefficiency of Lewis acids to catalyze it.
  • 53
    • 0034602374 scopus 로고    scopus 로고
    • For a review, see: Marson, C. A. Tetrahedron 2000, 56, 8779-8794.
    • (2000) Tetrahedron , vol.56 , pp. 8779-8794
    • Marson, C.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.