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Volumn 7, Issue 14, 2005, Pages 3077-3080

Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE;

EID: 22244446471     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051075g     Document Type: Article
Times cited : (88)

References (65)
  • 19
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  • 20
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    • For a recent report of nickel-catalyzed intermolecular alkyne insertions into cyclobutanones, see: Murakami, M.; Ashida, S.; Takanori, M. J. Am. Chem. Soc. 2005, 127, 6932-6933.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 6932-6933
    • Murakami, M.1    Ashida, S.2    Takanori, M.3
  • 21
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    • Transition metal mediated reductive coupling of alkynes and ketones (stoichiometric in transition metal): (a) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2544-2546
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  • 25
    • 0010077452 scopus 로고
    • Reductive cyclizations of alkynes and ketones promoted by samarium diiodide. Reviews: (a) Molander, G. A. Chem. Rev. 1992, 92, 29-68.
    • (1992) Chem. Rev. , vol.92 , pp. 29-68
    • Molander, G.A.1
  • 34
    • 0036432910 scopus 로고    scopus 로고
    • Catalytic intramolecular allene-ketone cyclizations: (a) Kang, S.-K.; Yoon, S.-K. Chem. Commun. 2002, 2634-2635.
    • (2002) Chem. Commun. , pp. 2634-2635
    • Kang, S.-K.1    Yoon, S.-K.2
  • 39
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    • Reviews: (a) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 48
    • 0035477040 scopus 로고    scopus 로고
    • For diastereoselective additions of alkenylzirconocenes to ketones and α-keto esters, respectively, see: (a) Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667-3670.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3667-3670
    • Chavez, D.E.1    Jacobsen, E.N.2
  • 50
    • 32744469904 scopus 로고    scopus 로고
    • note
    • P-Chiral ferrocenyl phosphines with other substitution patterns on this aromatic ring displayed reduced efficacy (e.g., 2-biphenyl, 28% yield, 18% ee; 2,5-dimethylphenyl, 76% yield, 50% ee; 2-i-Pr-phenyl, 13% yield, 70% ee).
  • 51
    • 32744468314 scopus 로고    scopus 로고
    • note
    • Superior yields were typically obtained in these reactions when conducted in the absence of an additional solvent. However, when solid ketones were employed, toluene was used as a cosolvent.
  • 52
    • 32744462445 scopus 로고    scopus 로고
    • note
    • Ketones containing two alkyl substituents, such as cyclohexyl methyl ketone or cyclopropyl methyl ketone, afforded coupling products in very low yield (< 10%), and α-keto esters were completely ineffective.
  • 53
    • 32744465108 scopus 로고    scopus 로고
    • note
    • The yield was improved by conducting this reaction at 35 °C: 55% yield, > 95:5 regioselectivity, 63% ee.
  • 54
    • 32744474534 scopus 로고    scopus 로고
    • note
    • Alkynes that lack an alkenyl substituent, such as 1-phenyl-1-propyne or 4-octyne, and 1,3-enynes bearing an aromatic substituent, such as 1-phenyl-3-buten-1-yne, did not undergo coupling under these conditions.
  • 55
    • 33845279009 scopus 로고
    • For leading references on related chiral 1,3-dienes in intermolecular Diels-Alder reactions, see: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257-3262.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3257-3262
    • Tripathy, R.1    Franck, R.W.2    Onan, K.D.3
  • 60
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    • In intramolecular Diels-Alder reactions, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
    • (1995) Chem. Rev. , vol.95 , pp. 1253-1277
    • Bols, M.1    Skrydstrup, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.