Stereodefined construction of trisubstituted alkenes by direct coupling reaction of allylating agents, alkynes, and organoboranes.
作者： Masahiro Fukushima , Daiki Takushima , Hideaki Satomura , Gen Onodera , Masanari Kimura
关键词:
摘要: Tandem reaction: The Pd-catalyzed three-component coupling reaction of an allylic alcohol, terminal alkyne, and organoborane to give (E)-1-substituted 2-alkyl-1,4-pentadienes, involving geminal allylation alkylation at the acetylenic carbon, is described. Bis-diene undergoes a similar multicomponent with acetylene organoborane, cyclization bis-π-allylpalladium, form trans-allyl pentadienyl cyclic heterocyclic compounds excellent regio- stereoselectivities (see scheme).
sci-hub.se 参考文章(36)
John Hooz, Richard Mortimer, A new route to di- and trisubstituted olefins via lithium trialkylalkynylborates Tetrahedron Letters. ,vol. 17, pp. 805- 808 ,(1976) , 10.1016/S0040-4039(00)92889-2
Yan Chen, Nan-Sheng Li, Min-Zhi Deng, None, The stereoselective allylation of lithium trialkylalkynylborates by allyl carbonate in the presence of Pd(PPh3)4 Tetrahedron Letters. ,vol. 31, pp. 2405- 2406 ,(1990) , 10.1016/S0040-4039(00)97373-8
Monica A. Kacprzynski, Amir H. Hoveyda, Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons Journal of the American Chemical Society. ,vol. 126, pp. 10676- 10681 ,(2004) , 10.1021/JA0478779
Yumi Yamaguchi, Mariko Hashimoto, Katsumi Tohyama, Masanari Kimura, Nucleophilic allylation of N,O-acetals with allylic alcohols promoted by Pd/Et3B and Pd/Et2Zn systems Tetrahedron Letters. ,vol. 52, pp. 913- 915 ,(2011) , 10.1016/J.TETLET.2010.12.064
Hidetaka Yatagai, The Reaction of Alkenylboranes with Palladium Acetate. Stereoselective Synthesis of Olefinic Derivatives Bulletin of the Chemical Society of Japan. ,vol. 53, pp. 1670- 1676 ,(1980) , 10.1246/BCSJ.53.1670
Norio Miyaura, Takashi Yano, Akira Suzuki, The palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with allylic or benzylic bromides. Convenient syntheses of 1,4-alkadienes and allybenzenes from alkynes via hydroboration Tetrahedron Letters. ,vol. 21, pp. 2865- 2868 ,(1980) , 10.1016/S0040-4039(00)78629-1
Hidetaka Yatagai, Yoshinori Yamamoto, Kazuhiro Maruyama, Protonolysis of alkenylboranes under neutral condition by treatment with catalytic amounts of palladium diacetate Journal of The Chemical Society, Chemical Communications. pp. 702- 703 ,(1978) , 10.1039/C39780000702
Naoki Ishida, Tomoya Miura, Masahiro Murakami, Stereoselective synthesis of trisubstituted alkenylboranes by palladium-catalysed reaction of alkynyltriarylborates with aryl halides. Chemical Communications. pp. 4381- 4383 ,(2007) , 10.1039/B710472C
Kiitiro Utimoto, Toshiki Furubayashi, Hitosi Nozaki, THE REACTION OF LITHIUM TRIBUTYL-1-PROPYNYLBORATE WITH OXIRANE. STEREOSELECTIVE SYNTHESIS OF (Z)- AND (E)-3-METHYL-3-OCTEN-1-OL Chemistry Letters. ,vol. 4, pp. 397- 400 ,(1975) , 10.1246/CL.1975.397
Go. Hata, Kuniyuki Takahashi, Akihisa Miyake, Palladium-catalyzed reactions of 1,3-dienes with active methylene compounds. II. Journal of Organic Chemistry. ,vol. 36, pp. 2116- 2123 ,(1971) , 10.1021/JO00814A018