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Volumn 10, Issue 9, 2008, Pages 1847-1850

Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; IMINE; MAGNESIUM; ORGANOMETALLIC COMPOUND; ZINC;

EID: 48849100571     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800478q     Document Type: Article
Times cited : (31)

References (30)
  • 7
    • 0034283587 scopus 로고    scopus 로고
    • For the use of silylated cyclohexadienes in radical chemistry, see: a
    • For the use of silylated cyclohexadienes in radical chemistry, see: (a) Studer, A.; Amrein, S, Angew. Chem., Int. Ed. 2000, 39, 3080.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 3080
    • Studer, A.1    Amrein, S.2
  • 15
    • 3142676522 scopus 로고    scopus 로고
    • Some recent examples on ally] metal additions: (a) Li, S.-W.; Batey, R. A. Chem. Commun. 2004, 1382.
    • Some recent examples on ally] metal additions: (a) Li, S.-W.; Batey, R. A. Chem. Commun. 2004, 1382.
  • 18
    • 34247857460 scopus 로고    scopus 로고
    • Allyl-zinc compounds have successfully been used in stereoselective allylations: (a) Ren, H.; Dunet, G.; Mayer, P.; Knochel, P J. Am. Chem. Soc. 2007, 129, 5376.
    • Allyl-zinc compounds have successfully been used in stereoselective allylations: (a) Ren, H.; Dunet, G.; Mayer, P.; Knochel, P J. Am. Chem. Soc. 2007, 129, 5376.
  • 19
    • 38349188554 scopus 로고    scopus 로고
    • Dunet, G.; Mayer, P.; Knochel, P Org. Lett. 2008, 10, 117. See also ref. 6c.
    • (b) Dunet, G.; Mayer, P.; Knochel, P Org. Lett. 2008, 10, 117. See also ref. 6c.
  • 20
    • 58149192300 scopus 로고    scopus 로고
    • An authentic sample of the diastereoisomer of symmetrical diene 6a was prepared for comparison. In the fraction of the inseparable isomers 14% combined yield, the diastereoisomer of 6a was identified and the diastereoselectivity was calculated to be 50:1
    • An authentic sample of the diastereoisomer of symmetrical diene 6a was prepared for comparison. In the fraction of the inseparable isomers (14% combined yield), the diastereoisomer of 6a was identified and the diastereoselectivity was calculated to be 50:1.
  • 22
    • 58149192613 scopus 로고    scopus 로고
    • An authentic sample of the diastereoisomer of symmetrical diene 6a was prepared for comparison. The 1H NMR showed characteristic signals which were used to identify the presence of the diastereoisomers of 6b-d. Due to signal overlap, the diastereosiomer ratio could not be determined for 6e and f. By GC analysis, the diastereoisomer of 6i was not identified. Selectivity of 6h was assigned in analogy
    • 1H NMR showed characteristic signals which were used to identify the presence of the diastereoisomers of 6b-d. Due to signal overlap, the diastereosiomer ratio could not be determined for 6e and f. By GC analysis, the diastereoisomer of 6i was not identified. Selectivity of 6h was assigned in analogy.
  • 23
    • 0033534429 scopus 로고    scopus 로고
    • Tang, T. P; Ellman, J. A J. Org. Chem. 1999, 64, 12.
    • Tang, T. P; Ellman, J. A J. Org. Chem. 1999, 64, 12.
  • 24
    • 0025895930 scopus 로고    scopus 로고
    • Stereoselective additions onto cis-imines: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C Tetrahedron Lett. 1991, 32. 5287.
    • Stereoselective additions onto cis-imines: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C Tetrahedron Lett. 1991, 32. 5287.
  • 26
    • 0034624432 scopus 로고    scopus 로고
    • Stereoselective syntheses: (a) Hayashi, T.; Ishigedani; M
    • Stereoselective syntheses: (a) Hayashi, T.; Ishigedani; M, J. Am. Chem. Soc. 2000, 122, 976.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 976


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.