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Volumn 66, Issue 16, 2010, Pages 3070-3089

Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates

Author keywords

1,3 Dipolar cycloaddition; Asymmetric synthesis; Carbonyl ylide; Chiral Lewis acid; Diazocarbonyl compound; Metal catalyst

Indexed keywords

1 DIAZO 2,5 PENTANEDIONE DERIVATIVE; 2 BENZOPYRYLIUM 4 OLATE; 2,3 DIHYDROFURAN; 2,6 BIS[4,5 DIPHENYL 2 OXAZOLINYL]PYRIDINE; ALCOHOL; ALKENE DERIVATIVE; BINAPHTHYLDIIMINE; BUTYL TERT BUTYLDIMETHYLSILYLKETENE ACETAL; CYCLIC CARBONYL YLIDE; CYCLOHEXYL VINYL ETHER; LEWIS ACID; METHYL 2 (2 DIAZO 1,3 DIOXOALKYL)BENZOATE; UNCLASSIFIED DRUG;

EID: 77949567244     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.095     Document Type: Article
Times cited : (49)

References (51)
  • 1
    • 77949567603 scopus 로고    scopus 로고
    • For books and reviewes, see
    • For books and reviewes, see:
  • 5
    • 77949569538 scopus 로고    scopus 로고
    • For representative examples, see
    • For representative examples, see
  • 31
    • 77949569945 scopus 로고    scopus 로고
    • note
    • Absolute configuration of the cycloadduct was not determined.
  • 32
    • 77949566894 scopus 로고    scopus 로고
    • note
    • The endo-adduct is defined as the product in which the more important substituent is on the opposite side of the epoxy bridge, whereas the exo-adduct indicates the product in which the more important substituent is on the same side as the epoxy bridge.
  • 33
    • 77949568701 scopus 로고    scopus 로고
    • note
    • 3: 88% yield, 55% ee.
  • 34
    • 77949570226 scopus 로고    scopus 로고
    • note
    • 3, reflux: 71% yield, 45% ee.
  • 40
    • 77949569422 scopus 로고    scopus 로고
    • note
    • Although the reason for the switch of the diastereoselectivity in this reaction is not clear at this point, flat structure of the carbonyl ylide for 2-benzopyryrium-4-olates may influence the endo/exo selectivity by inhibition of steric hindrance with vinyl esters. PM3 calculations (heat of formation) of 3f and 28f show that exo-cycloadducts are thermodynamically more stable than endo-cycloadducts, and endo-53a is slightly more stable (0.81 kcal/mol) than the corresponding exo-adduct.
  • 51
    • 77949570511 scopus 로고    scopus 로고
    • note
    • 2-lanthanoid metal complexes, however, the role of the catalyst is probably not only activation of the carbonyl ylide by coordination but also bring the reactants including allyl alcohol close together to achieve the appropriate transition state. The addition of basic inorganic salts may be attributed to the favored coordination of allyl alcohol to the catalyst by hydrogen bonding of allyl alcohol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.