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Volumn 122, Issue 28, 2000, Pages 6610-6618

Allylic alcohols via catalytic asymmetric epoxide rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 PYRROLIDINYL)METHYL 2 AZABICYCLO[2.2.1]HEPTANE; ALCOHOL DERIVATIVE; CARBOVIR; EPIBATIDINE; EPOXIDE; FARANAL; LASIOL; LITHIUM DIISOPROPYLAMIDE; UNCLASSIFIED DRUG;

EID: 0038673708     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000545t     Document Type: Article
Times cited : (95)

References (57)
  • 21
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    • Dilithiated norephedrine has been successfully applied in the isomerization of syn-4-(hydroxymethyl)cyclopentene oxides; see, e.g.: Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407-408.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 407-408
    • Hodgson, D.M.1    Gibbs, A.R.2
  • 24
    • 0000630997 scopus 로고    scopus 로고
    • and references therein. Enantiomerically pure 3 is routinely prepared in our laboratories, on scales up to 1 mol
    • See: Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530-2535 and references therein. Enantiomerically pure 3 is routinely prepared in our laboratories, on scales up to 1 mol.
    • (1998) J. Org. Chem. , vol.63 , pp. 2530-2535
    • Guijarro, D.1    Pinho, P.2    Andersson, P.G.3
  • 33
    • 0343565946 scopus 로고    scopus 로고
    • note
    • - (entry 2, Table 3). Deprotonation of 1e may lead to the formation of a mixture of diastereomeric lithium amides (i.e., having the methyl groups oriented either syn or anti relative to Li) which could, in principle, exhibit the opposite sense of enantioselectivity.
  • 34
    • 0028856838 scopus 로고
    • Some of the allylic alcohols in Table 4 are precursors to natural products and drugs. (a) Prostaglandin core unit (entries 2 and 3): see ref 5j. (b) Carbovir (entry 5), cf.: Asami, M.; Inoue, S. Tetrahedron 1995, 51, 11725-11730.
    • (1995) Tetrahedron , vol.51 , pp. 11725-11730
    • Asami, M.1    Inoue, S.2
  • 35
    • 0027634446 scopus 로고
    • (c) Lasiol, cf. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70. Faranal (entry 7), cf.: Mori, K.; Murata, N. Liebigs Ann. 1995, 2089-2092.
    • (1993) Bioorg. Med. Chem. , vol.1 , pp. 67-70
    • Kasai, T.1    Watanabe, H.2    Mori, K.3
  • 36
    • 0038304780 scopus 로고
    • (c) Lasiol, cf. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70. Faranal (entry 7), cf.: Mori, K.; Murata, N. Liebigs Ann. 1995, 2089-2092.
    • (1995) Liebigs Ann. , pp. 2089-2092
    • Mori, K.1    Murata, N.2
  • 38
    • 0028304224 scopus 로고
    • (d) Epibatidine (entry 10). cf.: Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron Lett. 1997, 38, 681-684. A subunit of manzamine A (entry 10), cf.: Kamenecka, T. M.; Overman, L. E. Tetrahedron Lett. 1994, 35, 4279-4282.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4279-4282
    • Kamenecka, T.M.1    Overman, L.E.2
  • 39
    • 0343130049 scopus 로고    scopus 로고
    • note
    • 2O in the absence of DBU gave an approximately 8/1 mixture of the allylic/bicyclic alcohols. The bicyclo[3.3.0]octan-2-ol thus obtained held 23% ee.
  • 41
    • 0344002192 scopus 로고    scopus 로고
    • note
    • For entry 4, a minor product, tentatively assigned as (1S)-2-methylene-1-cyclohexanol, was isolated in 11% yield (96% ee).


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