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Volumn , Issue 18, 2007, Pages 2819-2822

Chemoselective epoxidation of ene-ynamides: Intramolecular cyclopropanation induced by the intermediate α-oxocarbene

Author keywords

Cyclopropanation; Epoxidation; Oxirene; Ynamides; oxocarbene

Indexed keywords

CARBENOID;

EID: 36549002124     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990841     Document Type: Article
Times cited : (34)

References (34)
  • 5
    • 34547510627 scopus 로고    scopus 로고
    • For a review on gold-catalyzed reactions, see
    • For a review on gold-catalyzed reactions, see: Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
    • (2007) Chem. Rev , vol.107 , pp. 3180
    • Hashmi, A.S.K.1
  • 12
    • 0000504861 scopus 로고
    • Epoxidation of coordinated alkynes generate α-ketocarbene complexes, see
    • Epoxidation of coordinated alkynes generate α-ketocarbene complexes, see: Sun, S.; Edwards, J. O.; Sweigart, D. A.; D'Accolti, L.; Curci, R. Organometallics 1995, 14, 1545.
    • (1995) Organometallics , vol.14 , pp. 1545
    • Sun, S.1    Edwards, J.O.2    Sweigart, D.A.3    D'Accolti, L.4    Curci, R.5
  • 15
    • 33845201456 scopus 로고    scopus 로고
    • Oxidation of terminal alkynes with Oxone catalyzed by a Mn-porphyrin in the presence of primary amines as the ketene trap affords amides, see: Chan, W.-K, Ho, C.-M, Wong, M.-K, Che, C.-M. J. Am. Chem. Soc. 2006, 128, 14796
    • Oxidation of terminal alkynes with Oxone catalyzed by a Mn-porphyrin in the presence of primary amines as the ketene trap affords amides, see: Chan, W.-K.; Ho, C.-M.; Wong, M.-K.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 14796.
  • 16
    • 0002544558 scopus 로고
    • The α-oxocarbenes generated from cyclic α-diazoketones preferentially rearrange to α,β-unsaturated ketones or undergo Wolff rearrangement rather than transannular C-H insertions, see
    • The α-oxocarbenes generated from cyclic α-diazoketones preferentially rearrange to α,β-unsaturated ketones or undergo Wolff rearrangement rather than transannular C-H insertions, see: Ciabattoni, J.; Campbell, R. A.; Renner, C. A.; Concannon, P. W. J. Am. Chem. Soc. 1970, 92, 3826.
    • (1970) J. Am. Chem. Soc , vol.92 , pp. 3826
    • Ciabattoni, J.1    Campbell, R.A.2    Renner, C.A.3    Concannon, P.W.4
  • 24
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    • For a special issue devoted to the chemistry of ynamides, see
    • For a special issue devoted to the chemistry of ynamides, see: Tetrahedron 2006, 62, issue 16.
    • (2006) , vol.16 , Issue.62 and
    • Tetrahedron1
  • 27
    • 0000853980 scopus 로고    scopus 로고
    • (21 ) (a) The vanadium-catalyzed epoxidation of α- and β-allenyl alcohols has been descibed, see: Kim, S. J.; Cha, J. K. Tetrahedron Lett. 1988, 29, 5613.
    • (21 ) (a) The vanadium-catalyzed epoxidation of α- and β-allenyl alcohols has been descibed, see: Kim, S. J.; Cha, J. K. Tetrahedron Lett. 1988, 29, 5613.
  • 29
    • 36549071421 scopus 로고    scopus 로고
    • Representative Procedure: 2-Hydroxy-1, 1S*, 5R*)-2-(4-methylbenzenesulfonyl)-2-azabicyclo[3.1.0] hex-1-yl}ethanone (10) To a solution of ynamide 9 (136 mg, 0.486 mmol) in CH2Cl2 (5 mL) at 0°C were successively added VO(acac)2 (6.4 mg, 0.024 mmol, 0.05 equiv) and TBHP (0.220 mL, 5.5M in decane, 1.21 mmol, 2.5 equiv, After 0.5 hat r.t, the reaction mixture was cooled to 0°C and cautiously hydrolyzed with a 25% aqueous solution of Na2S2O3. After extraction with CH 2Cl2, the combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography (PE-EtOAc, 55:45) to afford 52 mg (40, of 10 as a colorless oil. IR: 3475, 1701, 1339, 1160, 1086, 903, 808, 666 cm-1. 1H NMR 300 MHz, CDCl3
    • 4S: C, 56.93; H, 5.80;N, 4.74. Found: C, 56.88; H, 5.93; N, 4.61.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.