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Volumn 2, Issue 8, 2000, Pages 1053-1056

Oxazoline N-oxide mediated [2 + 3] cycloadditions. Application to a formal synthesis of (+)-carpetimycin A

Author keywords

[No Author keywords available]

Indexed keywords

3A,7A DIHYDRO 8,8 DIMETHYL 4,7 METHANOCYCLOHEXO(1,2 D)OXAZOLE 3 OXIDE; 3A,7A-DIHYDRO-8,8-DIMETHYL-4,7-METHANOCYCLOHEXO(1,2-D)OXAZOLE-3-OXIDE; AMINE OXIDE; CARPETIMYCIN A; OXAZOLE DERIVATIVE; THIENAMYCIN DERIVATIVE;

EID: 0034689842     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005596+     Document Type: Article
Times cited : (19)

References (32)
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  • 7
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    • and references therein
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    • (d) For a review on oxazoline N-oxides [2 + 3] cycloadditions, see: Langlois, Y. Curr. Org. Chem. 1998, 2, 1-18.
    • (1998) Curr. Org. Chem. , vol.2 , pp. 1-18
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  • 11
    • 11544346529 scopus 로고    scopus 로고
    • (e) For a review on asymmetric 1,3-dipolar cycloadditions, see: Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-903.
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  • 13
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    • [2 + 3] cycloaddition between methyl 3-methyl 2-butenoate and nitrile oxide can be performed under forced conditions (large excess of dipolarophile, 130-140°C, 6.5 h), see ref 3a
    • [2 + 3] cycloaddition between methyl 3-methyl 2-butenoate and nitrile oxide can be performed under forced conditions (large excess of dipolarophile, 130-140°C, 6.5 h), see ref 3a.
  • 23
    • 0029114274 scopus 로고
    • Oxazoline N-oxide mediated [2 + 3] cycloadditions are genarally endo selective. An exo adduct was nevertehless obtained during cycloaddition with cyclopentadiene as dipolarophile as observed in other [2 + 3] cycloadditions with this particular dienophile, see: Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5523-5526
    • Berranger, T.1    Langlois, Y.2
  • 25
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    • Lane, C.F.1
  • 26
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    • 2, Pd-C, MeOH) induced isomerization from Z to E without any reduction
    • 2, Pd-C, MeOH) induced isomerization from Z to E without any reduction.
  • 27
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    • note
    • -3. Absolute configuration established by examination of Bijvoet pairs. Hydrogen atoms fitted at theoretical positions.
  • 29
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    • Crystallographic data for compound 17 has been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. (CCDC 139126)
    • (c) Crystallographic data for compound 17 has been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. (CCDC 139126).
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    • Ketol 20 can be transformed into hydroxylamino isoborneol 13 and reused, see: Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726.
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    • Dole, D.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.