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Volumn 71, Issue 5, 2006, Pages 2099-2106

Reactive ketimino radical acceptors: Intermolecular alkyl radical addition to imines with a phenolic hydroxyl group

Author keywords

[No Author keywords available]

Indexed keywords

AMINYL RADICAL; CARBON RADICAL; KETIMINE; PHENOLIC HYDROXYL GROUP;

EID: 33644652412     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052518x     Document Type: Article
Times cited : (54)

References (99)
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    • (2001) Radicals in Organic Synthesis , vol.1-2
  • 9
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    • For reviews on the radical cyclization of imines, see: (a) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
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    • Fallis, A.G.1    Brinza, I.M.2
  • 11
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    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttugart, New York
    • (c) Risch, N.; Arend, N. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttugart, New York, 1996; Vol. 3; pp 1833-2009.
    • (1996) Stereoselective Synthesis , vol.3 , pp. 1833-2009
    • Risch, N.1    Arend, N.2
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    • 33644649842 scopus 로고    scopus 로고
    • note
    • For the intermolecular enantioselective radical addition to aldimines, see refs 8b,c and 9f.
  • 79
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    • note
    • The preparation method of required starting materials 12-19 is reported in Supporting Information.
  • 80
    • 0001280351 scopus 로고
    • The [2 + 2] photocycloaddition of ketimine 12 was reported. See: Nishio, T.; Omote, Y. J. Org. Chem. 1985, 50, 1370.
    • (1985) J. Org. Chem. , vol.50 , pp. 1370
    • Nishio, T.1    Omote, Y.2
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    • The similar trends were observed in other radical reactions. In general, the phenyl-substituted box ligand B-zinc Lewis acid combination gives high selectivity, whereas the aliphatic substituted box ligands give high selectivity in combination with magnesium Lewis acid. See: (a) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9200
    • Sibi, M.P.1    Ji, J.2
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    • For few examples of chiral copper Lewis acid catalyzed radical reaction, see: Sibi, M. P.; Chen, J. J. Am. Chem. Soc. 2001, 123, 9472. Also see ref 8c.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9472
    • Sibi, M.P.1    Chen, J.2
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    • For discussion on the reversal of stereochemistry, see: (a) Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 719
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    • For a discussion of a square planar geometry model relative to copper, see: (a) Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 718
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    • note
    • A working hypothesis for the reversed sense of stereoinduction is shown in Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.