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Volumn 21, Issue 7, 2010, Pages 767-770

Enantioselective 6-endo-trig Wacker-type cyclization of 2-geranylphenols: Application to a facile synthesis of (-)-cordiachromene

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENE DERIVATIVE; CORDIACHROMENE; GERANIOL; ISOXAZOLINE DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

EID: 77955128212     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.060     Document Type: Article
Times cited : (37)

References (48)
  • 1
    • 2942609168 scopus 로고    scopus 로고
    • For reviews, see: (a)
    • For reviews, see: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285;
    • (2004) Chem. Rev. , Issue.104 , pp. 2285
    • Zeni, G.1    Larock, R.C.2
  • 21
    • 33751317736 scopus 로고    scopus 로고
    • For reviews, see: (a)
    • For reviews, see: (a) Hoffmann, R. W. Synthesis 2006, 3531;
    • (2006) Synthesis , pp. 3531
    • Hoffmann, R.W.1
  • 23
    • 0033063994 scopus 로고    scopus 로고
    • Since chiral chromenes are known to undergo photoracemization, the reaction apparatus was wrapped in aluminum foil to exclude light. For the photochemical racemization of chromenes, See: (a)
    • Since chiral chromenes are known to undergo photoracemization, the reaction apparatus was wrapped in aluminum foil to exclude light. For the photochemical racemization of chromenes, See: (a) Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321;
    • (1999) J. Org. Chem. , vol.64 , pp. 5321
    • Wipf, P.1    Weiner, W.S.2
  • 37
    • 85030590997 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum using p-hydroxyacetophenone as an internal standard. The residue was purified by preparative TLC in the dark to give dihydrobenzofuran 2 and chromene 3.
  • 44
    • 85030587463 scopus 로고    scopus 로고
    • note
    • We indeed observed photoracemization of the products 3b-k: for example, for 3k, 55% ee was diminished to 45% ee after 24 h upon irradiation with a (room) light.
  • 47
    • 85030578837 scopus 로고    scopus 로고
    • note
    • Both stepwise addition of p-benzoquinone and the use of a combination of O2 with Cu co-catalyst as the oxidant were ineffective.
  • 48
    • 85030576470 scopus 로고    scopus 로고
    • note
    • 3, 95% ee)}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.