Catalytic Asymmetric Synthesis of Allylsilanes through Rhodium/Chiral Diene-Catalyzed 1,4-Addition of Alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes

作者: Ryo Shintani , Yoshitaka Ichikawa , Tamio Hayashi , Jinshui Chen , Yoshiaki Nakao

DOI: 10.1021/OL702125Q

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摘要: A new synthetic method of chiral allylsilanes has been developed through a rhodium-catalyzed asymmetric 1,4-addition alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes to β-silyl α,β-unsaturated ketones. By employing (S,S)-Ph-bod* as ligand, range alkenyl nucleophiles have installed these substrates in high yield and enantiomeric excess. The resulting can be used for stereoselective intramolecular allylation reactions control two contiguous tertiary quaternary stereocenters.

参考文章(45)
Tamio Hayashi, Keiji Kabeta, Tsunehiro Yamamoto, Kohei Tamao, Makoto Kumada, Optically active cyclic allylsilanes: Preparation by asymmetric hydrosilylation and anti stereochemistry in SE' reactions☆ Tetrahedron Letters. ,vol. 24, pp. 5661- 5664 ,(1983) , 10.1016/S0040-4039(00)94167-4
Tamio Hayashi, Hiroshi Iwamura, Yasuhiro Uozumi, Asymmetric synthesis of allylsilanes by palladium-catalyzed asymmetric reduction of allylic carbonates with formic acid Tetrahedron Letters. ,vol. 35, pp. 4813- 4816 ,(1994) , 10.1016/S0040-4039(00)76975-9
Tamio Hayashi, Akira Ohno, Shi-jie Lu, Yonetatsu Matsumoto, Emiko Fukuyo, Kazunori Yanagi, Optically-Active Ruthenocenylbis(Phosphines) - New Efficient Chiral Phosphine-Ligands for Catalytic Asymmetric Reactions Journal of the American Chemical Society. ,vol. 116, pp. 4221- 4226 ,(1994) , 10.1021/JA00089A011
Tamio Hayashi, Mitsuo Konishi, Hiroshi Ito, Makoto Kumada, OPTICALLY ACTIVE ALLYLSILANES. 1. PREPARATION BY PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING AND ANTI STEREOCHEMISTRY IN ELECTROPHILIC SUBSTITUTION REACTIONS Journal of the American Chemical Society. ,vol. 104, pp. 4962- 4963 ,(1982) , 10.1021/JA00382A045
Norihito Tokunaga, Yusuke Otomaru, Kazuhiro Okamoto, Kazuhito Ueyama, Ryo Shintani, Tamio Hayashi, C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines Journal of the American Chemical Society. ,vol. 126, pp. 13584- 13585 ,(2004) , 10.1021/JA044790E
Yoshiaki Nakao, Hidekazu Imanaka, Akhila K. Sahoo, Akira Yada, Tamejiro Hiyama, Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: an entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction. Journal of the American Chemical Society. ,vol. 127, pp. 6952- 6953 ,(2005) , 10.1021/JA051281J
Graeme R. Jones, Yannick Landais, The oxidation of the carbon-silicon bond Tetrahedron. ,vol. 52, pp. 7599- 7662 ,(1996) , 10.1016/S0040-4020(96)00038-5