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Volumn 63, Issue 23, 1998, Pages 8470-8474

Palladium catalyzed regioselective β-acetonation-α-allylation of activated olefins in one shot

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALDEHYDE; ALKENE; MALONONITRILE; PALLADIUM;

EID: 0032514974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981719g     Document Type: Article
Times cited : (43)

References (55)
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    • (1987) Palladium Reagents in Organic Synthesis , pp. 117
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    • John Wiley & Sons: Chichester
    • For general reviews: (a) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, p 799. (b) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: London, 1987; p 117. (c) Tsuji, J. Palladium Reagents and Catalysts, John Wiley & Sons: Chichester, 1995; p 290. (d) Trost, B. M. Angew. Chem. 1995, 107, 285; Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
    • (1995) Palladium Reagents and Catalysts , pp. 290
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    • The palladium(II) enolate complex may be formally expressed in three different structures: (1) palladiun(II) enolate, (2) oxa-π-allylpalladium(II), and (3) 2-oxoalkylpalladium(II) complex. See also: (a) Tsuda, T.; Chujo, Y.; Nishi, S.-I.; Tawara, K.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 6381.
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    • Reference 10c
    • (b) Reference 10c.
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    • It was reported that palladium catalysts induced decarboxylation of allylic β-keto carboxylates to produce α-allylic ketones via a π-allylpalladium enolate; ref 13a
    • It was reported that palladium catalysts induced decarboxylation of allylic β-keto carboxylates to produce α-allylic ketones via a π-allylpalladium enolate; ref 13a.
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    • note
    • 2 did not induce the desired reaction.
  • 46
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    • Boeckman, R. K., Jr.; Ko, S. S. J. Am. Chem. Soc. 1982, 104, 1033. See also: Shim, J.-G.; Yamamoto, Y. J. Org. Chem. 1998, 63, 3067.
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    • Reductive elimination of Pd(0) from π-allylpalladium complexes, in which a π-allyl group and a stabilized carbanion are coordinated to palladium, is known. (a) Takahashi, Y.; Sakai, S.; Ishii, Y. Chem. Commun. 1967, 1092.
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    • (d) Reference 12.
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    • note
    • 2 occupied in 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.