Nickel-catalyzed homoallylation of adelhydes and ketones with 1,3- dienes and complementary promotion by diethylzinc or triethylborane

Angewandte Chemie - International Edition

Volumn 38, Issue 3, 1999, Pages 397-400

  Kimura, Masanari ^a   Fujimatsu, Hidetaka ^a   Ezoe, Akihiro ^a   Shibata, Kazufumi ^a   Shimizu, Masamichi ^a   Matsumoto, Satoru ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Aldehydes; Alkylations; Ketones; Nickel; Zinc

Indexed keywords

ALDEHYDE; ALKADIENE; BORANE DERIVATIVE; CARBONYL DERIVATIVE; ISOPRENE; KETONE; NICKEL; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033082780     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990201)38:3<397::AID-ANIE397>3.0.CO;2-Y     Document Type: Article

References (18)

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9. For NiH-mediated stoichiometric homoallylation of carbonyl compounds with 1,3-dienes, see a) Y. Sato, M. Takimoto, M. Mori, Synlett 1998, 734-736, and references therein: for transition metal catalyzed allylation with 1,3-dienes, see b) M. Takimoto, Y. Hiraga, Y. Sato, M. Mori, Tetrahedron Lett. 1998, 39, 4543-4546, and references therein: c) K. Kitayama, H. Tsuji, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 4169-4172; d) Y. Gao, H. Urabe, F. Sato, J. Org. Chem. 1994, 59, 5521-5523.
10. For NiH-mediated stoichiometric homoallylation of carbonyl compounds with 1,3-dienes, see a) Y. Sato, M. Takimoto, M. Mori, Synlett 1998, 734-736, and references therein: for transition metal catalyzed allylation with 1,3-dienes, see b) M. Takimoto, Y. Hiraga, Y. Sato, M. Mori, Tetrahedron Lett. 1998, 39, 4543-4546, and references therein: c) K. Kitayama, H. Tsuji, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 4169-4172; d) Y. Gao, H. Urabe, F. Sato, J. Org. Chem. 1994, 59, 5521-5523.
11. For NiH-mediated stoichiometric homoallylation of carbonyl compounds with 1,3-dienes, see a) Y. Sato, M. Takimoto, M. Mori, Synlett 1998, 734-736, and references therein: for transition metal catalyzed allylation with 1,3-dienes, see b) M. Takimoto, Y. Hiraga, Y. Sato, M. Mori, Tetrahedron Lett. 1998, 39, 4543-4546, and references therein: c) K. Kitayama, H. Tsuji, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 4169-4172; d) Y. Gao, H. Urabe, F. Sato, J. Org. Chem. 1994, 59, 5521-5523.
12. For NiH-mediated stoichiometric homoallylation of carbonyl compounds with 1,3-dienes, see a) Y. Sato, M. Takimoto, M. Mori, Synlett 1998, 734-736, and references therein: for transition metal catalyzed allylation with 1,3-dienes, see b) M. Takimoto, Y. Hiraga, Y. Sato, M. Mori, Tetrahedron Lett. 1998, 39, 4543-4546, and references therein: c) K. Kitayama, H. Tsuji, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 4169-4172; d) Y. Gao, H. Urabe, F. Sato, J. Org. Chem. 1994, 59, 5521-5523.
13. A similar electron relay was suggested for the nickel(0)-catalyzed reductive coupling of aldehydes and alkynes to give allylic alcohols: E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065-9066.
14. M. Kimura, A. Ezoe, K. Shibata, Y. Tamaru, J. Am. Chem. Soc. 1998, 120, 4033-4034.
15. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 735.
16. Since the cyclic dienes 1,3-cyclohexadiene and 1,3-cyclooctadiene give intractable mixtures of products, the s-trans-dienenickel(0) complex is assumed to be a reactive species.
17. 5-Vinyl-2-oxa-1-palladacyclopentanes, the palladium analogues of IV. undergo ring opening to give mixtures of dienes and carbonyl compounds, the formal reverse of the present reaction: H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449-2451; Angew. Chem. Int. Ed. Engl. 1997, 36, 2352-2354.
18. 5-Vinyl-2-oxa-1-palladacyclopentanes, the palladium analogues of IV. undergo ring opening to give mixtures of dienes and carbonyl compounds, the formal reverse of the present reaction: H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449-2451; Angew. Chem. Int. Ed. Engl. 1997, 36, 2352-2354.