Cyclization/acylation reactions by nickel-catalyzed reactions of 1,6-ynal and 1,6-enyne derivatives with acylzirconocene chloride

Tetrahedron Letters

Volumn 47, Issue 13, 2006, Pages 2201-2204

  Saito, Akio ^a   Oka, Yusuke ^b   Nozawa, Yohei ^a   Hanzawa, Yuji ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

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

Author keywords

Acylation; Acylzirconocene chloride complex; Cyclization; Nickel catalyst

Indexed keywords

CYCLOPENTANE DERIVATIVE; NICKEL; ORGANOMETALLIC COMPOUND;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY;

EID: 33344472825     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.101     Document Type: Article

References (22)

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17. An attempted reaction of N-benzyl compound instead of N-Ts compound 3b afforded a complex reaction mixture even under ice- or dry ice-acetone cooling conditions.
18. About the Ni catalyst, Ni(0) or Ni(II) is considered to be possible. However, Ni(0) species would be considered a catalyst in the present experiments, since (i) the formation of a small amount of 1,2-diketone, which is derived from the coupling of 1 by the use of Ni(II) catalyst followed by the reductive elimination of Ni(0), and (ii) the efficient catalytic activity of Ni(0) catalyst have been observed. Ni-catalyzed reactions of n-octyne with 1 under the identical conditions did not show the acylation reaction. Therefore the following sequential mechanism is considered less possible; (i) the primary formation of acyl Ni species by the reaction of 1 and Ni catalyst, (ii) the addition of the acyl Ni to the terminal alkynyl group of 2 or 3 giving a vinyl metal species, and (iii) an intramolecular attack of the vinyl metal to the carbonyl or alkene. Efficient Ni-catalyzed additions of acyltin compounds to alkynes have been reported. See: Shirakawa, E.; Nakao, Y.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 2000, 122, 9030.
19. 3-catalyzed reaction of 3a. See: H.-Y. Rhyoo, B.Y. Lee, H.K.B. Yu, and Y.K. Chung J. Mol. Catal. 92 1994 41
20. The formation of oxanickelacycle 10 (Y = O) has been reported for the Ni(0)-catalyzed reaction of 1,6-ynals. See: E. Oblinger, and J. Montgomery J. Am. Chem. Soc. 119 1997 9065
21. 2 has been reported. See Ref. 13.
22. It is not clear for us at this moment to explain why gem-benzyloxymethyl compounds 2b and 3d showed the isomerization.