RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012; 44(15): 2333-2339
DOI: 10.1055/s-0031-1290764
DOI: 10.1055/s-0031-1290764
practical synthetic procedures
Regio- and Stereoselective Multicomponent Coupling Reaction of Alkynes and Dimethylzinc Involving Allylnickelacycles
Weitere Informationen
Publikationsverlauf
Received: 10. Februar 2012
Accepted: 17. Februar 2012
Publikationsdatum:
12. April 2012 (online)
Abstract
Nickel catalyzes the multicomponent coupling reaction of vinyl epoxides, alkynes, and dimethylzinc to provide hepta-2,5-dienyl alcohols as a mixture of E- and Z-isomers in high yields. Vinylcyclopropane participates in a similar multicomponent coupling reaction to afford dimethyl α-(hepta-2,5-dienyl)malonates with excellent E-stereoselectivity.
-
References
- 1a Jun C.-H. Chem. Soc. Rev. 2004; 33: 610
- 1b Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
- 2a Suginome M, Matsuda T, Yoshimoto T, Ito Y. Organometallics 2002; 21: 1537
-
2b Zuo G, Louie J. Angew. Chem. Int. Ed. 2004; 43: 2277
-
2c Zuo G, Louie J. J. Am. Chem. Soc. 2005; 127: 5798
-
2d Liu L, Montgomery J. J. Am. Chem. Soc. 2006; 128: 5348
- 2e Ogoshi S, Nagata M, Kurosawa H. J. Am. Chem. Soc. 2006; 128: 5350
- 2f Bowman RK, Jonson JS. Org. Lett. 2006; 8: 573
- 2g Kimura M, Tamaru Y. Top. Curr. Chem. 2007; 279: 173
- 2h Ogata K, Atsuumi Y, Shimada D, Fukuzawa S.-i. Angew. Chem. Int. Ed. 2011; 50: 5896
- 3a Kimura M, Ezoe A, Mori M, Tamaru Y. J. Am. Chem. Soc. 2005; 127: 201
- 3b Kojima K, Kimura M, Tamaru Y. Chem. Commun. 2005; 4717
- 3c Kimura M, Kojima K, Tatsuyama Y, Tamaru Y. J. Am. Chem. Soc. 2006; 128: 6332
- 3d Kimura M, Mori M, Mukai R, Kojima K, Tamaru Y. Chem. Commun. 2006; 3813
- 3e Kojima K, Kimura M, Ueda S, Tamaru Y. Tetrahedron 2006; 62: 7512
- 4a Kimura M, Tatsuyama Y, Kojima K, Tamaru Y. Org. Lett. 2007; 9: 1871
- 4b Kimura M, Togawa M, Tatsuyama Y, Matsufuji K. Tetrahedron Lett 2009; 50: 3982
- 5 Nakamura T, Mori T, Togawa M, Kimura M. Heterocyles 2012; 84: 339
-
6a Ikeda S.-i, Cui D.-M, Sato Y. J. Org. Chem. 1994; 59: 6877
- 6b Ikeda S.-i, Miyashita H, Sato Y. Organometallics 1998; 17: 4316
-
6c Cui D.-M, Tsuzuki T, Miyake K, Ikeda S.-i, Sato Y. Tetrahedron 1998; 54: 1063
- 7 Ikeda S, Obara H, Tsuchida E, Shirai N, Odashima K. Organometallics 2008; 27: 1645
- 8 Mori T, Nakamura T, Kimura M. Org. Lett. 2011; 13: 2266
- 9 Parsons AT, Campbell MJ, Johnson JS. Org. Lett. 2008; 10: 2541