Pd-catalyzed acylation of α,β-ynone with acylzirconocene chloride and one-pot formation of cyclopentenone derivatives

Tetrahedron Letters

Volumn 42, Issue 9, 2001, Pages 1737-1739

  Hanzawa, Yuji ^a   Kakuuchi, Akito ^a   Yabe, Masaya ^a   Narita, Kensuke ^a   Tabuchi, Nobuhito ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ACYLZIRCONOCENE CHLORIDE DERIVATIVE; ALPHA YNONE DERIVATIVE; BETA ACYLZIRCONOCENE CHLORIDE DERIVATIVE; BETA YNONE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; ZIRCONOCENE;

ACYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0035951942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)02342-X     Document Type: Article

References (14)

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11. It has been reported that the triphenylphosphine isomerizes α,β-ynone to conjugated dienone via allenyl ketone, see: Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1980, 102, 1333. Thus, it might be doubted that the Michael addition of 1 to the allenyl ketone intermediate followed by isomerization to 3. However, in our case, this possibility is denied since t-Bu- or phenyl-substituted ynone (2b, c or d) yielded 3.
12. 4 (10 mol%) gave 7b in 52% yield.
13. For Nazarov reaction, see: Denmark S.E. Trost B.M., Fleming I., Paquette L.A. Comprehensive Organic Synthesis. 5:1991;751 Pergamon, Oxford.
14. Although the intramolecular Michael addition is also a plausible mechanism, we believe that the concerted process is a prevailing process since the reactions of α,β-enone with 6 did not give cyclopentane compounds under 1,4-acylation conditions, see Ref. 2.