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Volumn 13, Issue 19, 2011, Pages 5188-5191

Oxazolidine synthesis by complementary stereospecific and stereoconvergent methods

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE; OXAZOLIDINE;

EID: 80054760159     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202068p     Document Type: Article
Times cited : (70)

References (39)
  • 1
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    • A general review of the tetrahydroisoquinoline natural products and analogs: Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
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    • Scott, J.D.1    Williams, R.M.2
  • 4
    • 43949088503 scopus 로고    scopus 로고
    • For Cu(II) catalyzed aminohydroxylation of styrenes with oxaziridines to provide 1,3-oxazolidines, with up to 2.5:1 dr and 89% ee
    • For Cu(II) catalyzed aminohydroxylation of styrenes with oxaziridines to provide 1,3-oxazolidines, with up to 2.5:1 dr and 89% ee, see: Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 6610.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 6610
    • Michaelis, D.J.1    Ischay, M.A.2    Yoon, T.P.3
  • 10
    • 0034143235 scopus 로고    scopus 로고
    • Racemic synthesis of 1,3-oxazolidines from imines and vinyl epoxides
    • Racemic synthesis of 1,3-oxazolidines from imines and vinyl epoxides: Shim, J.-G.; Yamamoto, Y. Heterocycles 2000, 52, 885-895.
    • (2000) Heterocycles , vol.52 , pp. 885-895
    • Shim, J.-G.1    Yamamoto, Y.2
  • 22
    • 80054768777 scopus 로고    scopus 로고
    • Phosphine Ligands (e.g., BINAP, dipamp) Inhibit the Reaction
    • Phosphine ligands (e.g., BINAP, dipamp) inhibit the reaction.
  • 30
    • 84856525703 scopus 로고    scopus 로고
    • Monodentate phosphines provided only crotonaldehyde, resulting from β-hydride elimination. Bidentate ligands with bite angles similar to dppe formed most efficient Ni catalysts for oxazolidine formation
    • Monodentate phosphines provided only crotonaldehyde, resulting from β-hydride elimination. Bidentate ligands with bite angles similar to dppe formed most efficient Ni catalysts for oxazolidine formation.
  • 31
    • 84856523718 scopus 로고    scopus 로고
    • 1H NMR. In the absence of Lewis acid, no reaction is observed
    • 1H NMR. In the absence of Lewis acid, no reaction is observed.
  • 34
    • 80054740814 scopus 로고    scopus 로고
    • Under the optimized conditions with Ni catalyst a series of aryl imine electrophiles reacted in up to 65% ee See Supporting Information
    • Under the optimized conditions with Ni catalyst a series of aryl imine electrophiles reacted in up to 65% ee See Supporting Information.
  • 35
    • 77956225392 scopus 로고    scopus 로고
    • Palladium-catalyzed synthesis of trans-1,3-oxazolidines in up to 2.3:1 ratio as a racemic mixture
    • Palladium-catalyzed synthesis of trans-1,3-oxazolidines in up to 2.3:1 ratio as a racemic mixture: Chen, D.; Chen, X.; Du, T.; Kong, L.; Zhen, R.; Zhen, S.; Wen, Y.; Zhu, G. Tetrahedron Lett. 2010, 51, 5131.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 5131
    • Chen, D.1    Chen, X.2    Du, T.3    Kong, L.4    Zhen, R.5    Zhen, S.6    Wen, Y.7    Zhu, G.8
  • 36
    • 80054716695 scopus 로고    scopus 로고
    • Isoprene monoxide provided 98% yield and 62% ee. See Supporting Information for details
    • Isoprene monoxide provided 98% yield and 62% ee. See Supporting Information for details.
  • 39
    • 85050296727 scopus 로고
    • Several scenarios that involve a kinetic resolution of the vinyl epoxide are possible. For a detailed discussion of such kinetic resolution reactions
    • Several scenarios that involve a kinetic resolution of the vinyl epoxide are possible. For a detailed discussion of such kinetic resolution reactions, see: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.