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Volumn 12, Issue 9, 2010, Pages 1980-1983

Enantioselective synthesis of planar-chiral 1, n -dioxa[ n ]paracyclophanes via catalytic asymmetric ortho -Lithiation

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

EID: 77951865025     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100444u     Document Type: Article
Times cited : (44)

References (52)
  • 1
    • 0003559584 scopus 로고
    • For reviews, see:, Vögtle, F., Ed.; Wiley: Chichester
    • For reviews, see: Cyclophane Chemistry; Vögtle, F., Ed.; Wiley: Chichester, 1993.
    • (1993) Cyclophane Chemistry
  • 2
    • 3242887372 scopus 로고    scopus 로고
    • Gleither, R. and Hopf, H., Eds.; Wiley: Chichester
    • Modern Cyclophane Chemistry; Gleither, R. and Hopf, H., Eds.; Wiley: Chichester, 2004.
    • (2004) Modern Cyclophane Chemistry
  • 11
    • 0142009578 scopus 로고    scopus 로고
    • For a review of [2.2]paracyclophane derivatives for asymmetric syntheses, see
    • For a review of [2.2]paracyclophane derivatives for asymmetric syntheses, see: Gibson, S. E.; Knight, J. D. Org. Biomol. Chem. 2003, 1, 1256-1269
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1256-1269
    • Gibson, S.E.1    Knight, J.D.2
  • 15
    • 70349912194 scopus 로고    scopus 로고
    • It is not an enantioselective synthesis, but enantiomerically pure paracyclophanes have been recently synthesized from hydrogen-bond controlled axially chiral substrates using metathesis
    • It is not an enantioselective synthesis, but enantiomerically pure paracyclophanes have been recently synthesized from hydrogen-bond controlled axially chiral substrates using metathesis: Mori, K.; Ohmori, K.; Suzuki, K. Angew. Chem., Int. Ed. 2009, 48, 5638-5641
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5638-5641
    • Mori, K.1    Ohmori, K.2    Suzuki, K.3
  • 23
    • 77951830918 scopus 로고    scopus 로고
    • For examples of lithiation using a catalytic amount of chiral diamines, see
    • For examples of lithiation using a catalytic amount of chiral diamines, see
  • 27
    • 77951843025 scopus 로고    scopus 로고
    • Note
    • For examples of enantioselective lithiation using a catalytic amount of chiral diamines and a stoichiometric amount of achiral amines including lithium amide, see
  • 39
    • 77951796707 scopus 로고    scopus 로고
    • Enantioselective synthesis of a planar-chiral ferrocene via asymmetric deprotonation using a catalytic amount of a chiral diamine was reported; see ref 8a
    • Enantioselective synthesis of a planar-chiral ferrocene via asymmetric deprotonation using a catalytic amount of a chiral diamine was reported; see ref 8a.
  • 40
    • 77951855911 scopus 로고    scopus 로고
    • Enantiomeric resolution is accomplished in the case of monosubstituted [11]paracyclophanes at room temperature; see
    • Enantiomeric resolution is accomplished in the case of monosubstituted [11]paracyclophanes at room temperature; see
  • 44
    • 77951866947 scopus 로고    scopus 로고
    • In the case of n- BuLi and t -BuLi, only a trace amount of 2aa was obtained
    • In the case of n- BuLi and t -BuLi, only a trace amount of 2aa was obtained.
  • 51
    • 77951836614 scopus 로고    scopus 로고
    • Note
    • 4 and evaporated under reduced pressure. The resulting residue was purified by PTLC to give 2aa.
  • 52
    • 77951828374 scopus 로고    scopus 로고
    • Note
    • The absolute configuration was determined by comparison of the sign of optical rotation of dibromodioxa[12]paracyclophane with that in the literature; (2d) see Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.