Nickel-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,ω-Ene-Diene, and Acetone: Synthesis of 1,2-Disubstituted Cycloalkanes

Masanari Kimura; Keisuke Kojima; Yoshinao Tamaru

doi:10.1055/s-2004-834908

SPECIALTOPIC

Nickel-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,ω-Ene-Diene, and Acetone: Synthesis of 1,2-Disubstituted Cycloalkanes

Masanari Kimura^a, Keisuke Kojima^b, Yoshinao Tamaru*^b
^a Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan
^b Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan
Fax: +81(958)192677; e-Mail: tamaru@net.nagasaki-u.ac.jp;

Abstract

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Abstract

Under nickel catalysis, 1,3,8-nonatrienes and 1,3,9-decatrienes 3 react at room temperature with dimethylzinc and acetone at the alkene and diene termini, respectively, providing 1,2-disubstituted cycloalkanes 4 in good yield. The stereoselectivities of 4 provide useful information about the mechanistic frameworks for the present reaction and related cyclization reaction of ω-dienynes 1.

Keywords

nickel - organozinc - catalysis - cyclization - diene

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References

<A NAME="RC05304SS-1A">1a</A> Ezoe A. Kimura M. Inoue T. Mori M. Tamaru Y. Angew. Chem. Int. Ed. 2002, 41: 2784

<A NAME="RC05304SS-1B">1b</A> Kimura M. Ezoe A. Mori M. Tamaru Y. J. Am. Chem. Soc. 2004, in press

Protocols for this type of Ni-catalyzed addition of dienes to aldehydes:

<A NAME="RC05304SS-2A">2a</A> Kimura M. Ezoe A. Shibata K. Tamaru Y. J. Am. Chem. Soc. 1998, 120: 4033

<A NAME="RC05304SS-2B">2b</A> Kimura M. Fujimatsu H. Ezoe A. Shibata K. Shimizu M. Matsumoto S. Tamaru Y. Angew. Chem. Int. Ed. 1999, 38: 397

<A NAME="RC05304SS-2C">2c</A> Sato Y. Takimoto M. Mori M. J. Am. Chem. Soc. 2000, 122: 1624

<A NAME="RC05304SS-2D">2d</A> Shibata K. Kimura M. Shimizu M. Tamaru Y. Org. Lett. 2001, 3: 2181

<A NAME="RC05304SS-2E">2e</A> Kimura M. Ezoe A. Tanaka S. Tamaru Y. Angew. Chem. Int. Ed. 2001, 40: 3600

<A NAME="RC05304SS-2F">2f</A> Sato Y. Sawaki R. Saito N. Mori M. J. Org. Chem. 2002, 67: 656

<A NAME="RC05304SS-2G">2g</A> Kimura M. Miyachi A. Kojima K. Tanaka S. Tamaru Y. J. Am. Chem. Soc. 2004, in press

Protocols of this type Ni-catalyzed oxidative cyclization of alkynes and alkenes:

<A NAME="RC05304SS-3A">3a</A> Chowdhury SK. Amarasinghe KKD. Heeg MJ. Montgomery J. J. Am. Chem. Soc. 2000, 122: 6775

<A NAME="RC05304SS-3B">3b</A> Mahandru GM. Skauge ARL. Chowdhury SK. Amarasinghe KKD. Heeg MJ. Montgomery J. J. Am. Chem. Soc. 2003, 125: 13481

<A NAME="RC05304SS-3C">3c</A> Review: Montgomery J. Angew. Chem. Int. Ed. 2004, 43: 3890

<A NAME="RC05304SS-3D">3d</A> Tamao K. Kobayashi K. Ito Y. Synlett 1992, 539

<A NAME="RC05304SS-4">4</A> Eliel EL. Wilen SH. Stereochemistry of Organic Compounds John Wiley & Sons; New York: 1994. p.776

<A NAME="RC05304SS-5">5</A> To the best of our knowledge, this is the first example of transition-metal catalyzed cyclization of 1,3,8-nonatrienes and 1,3,9-decatrienes (3) except the transition-metal catalyzed Diels-Alder reaction: O’Mahony DJR. Belanger DB. Livinghouse T. Synlett 1998, 443

<A NAME="RC05304SS-6">6</A> Günter H. NMR Spectroscopy 2nd Ed: John Wiley & Sons; Chichester: 1995.

<A NAME="RC05304SS-7A">7a</A> Kimura M. Matsuo S. Shibata K. Tamaru Y. Angew. Chem. Int. Ed. 1999, 38: 3386

<A NAME="RC05304SS-7B">7b</A> Kimura M. Shibata K. Koudahashi Y. Tamaru Y. Tetrahedron Lett. 2000, 41: 6789

<A NAME="RC05304SS-7C">7c</A> Shibata K. Kimura M. Kojima K. Tanaka S. Tamaru Y. J. Organomet. Chem. 2001, 624: 348