Hosomi Sakurai反應是指在路易斯酸催化下各種親電試劑和烯丙基三甲基硅烷反應進行烯丙基化的反應。此反應中Lewis酸是反應能夠進行的關鍵。

反應機理

Note: 硅烷對β 碳正離子有穩定作用 (β effect)

在一些反應中只需要催化量的Lewis酸就能進行反應，但反應中要使用烯丙基氯硅烷而不是烯丙基三甲基硅烷：

A. Fürstner, D. Voigtl?nder, Synthesis, 2000, 959-969.

最新文獻

Silver-Catalyzed Asymmetric Sakurai-Hosomi Allylation of Ketones
M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc., 2005, 127, 14556-14557.

Synthesis of Homoallyl Ethers via Allylation of Acetals in Ionic Liquids Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
H. M. Zerth, N. M. Leonard, R. S. Mohan, Org. Lett., 2003, 5, 55-57.

o-Benzenedisulfonimide as a Reusable Br?nsted Acid Catalyst for Hosomi-Sakurai Reactions
M. Barbero, S. Bazzi, S. Cadamuro, S. Dughera, C. Piccinini, Synthesis, 2010, 315-319.

Efficient Br?nsted Acid Catalyzed Hosomi-Sakurai Reaction of Acetals
D. Kampen, B. List, Synlett, 2006, 2589-2592.

Microwave-Assisted Allylation of Acetals with Allyltrimethylsilane in the Presence of CuBr
M. E. Jung, A. Maderna, J. Org. Chem., 2004, 69, 7755-7757.

METHOX: A New Pyridine N-Oxide Organocatalyst for the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes
A. V. Malkov, M. Bell, F. Castelluzzo, P. Kocovsky, Org. Lett., 2005, 7, 3219-3222.

A General Catalytic Allylation Using Allyltrimethoxysilane
S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2002, 124, 6536-6537.

FeSO₄·7H₂O-Catalyzed Four-Component Synthesis of Protected Homoallylic Amines
Q.-Y. Song, B.-L. Yang, S.-K. Tian, J. Org. Chem., 2007, 72, 5407-5410.

在非鹵化溶劑中，增強的路易斯酸體系可以促進醇與硅烷基親核試劑之間的直接偶聯反應。 與酮和乙酰氧基化合物相比，對羥基有高度選擇性的烯丙基化反應已被證實。 齋藤，y. 西本，m. 安田，a. baba，j. org。 Chem. ，2006,71,8516-8522.

5 mol% 的三溴化銦在溫和條件下催化炔基硅烷和烯丙基三甲基硅烷的選擇性偶聯反應，得到相應的,-乙炔基酮和,-不飽和酮。 S. yadav，b.v.s. reddy，m. sridhar reddy，g. parimala，synthesis，2003,2390-2394.

Generation of Cations from Alkoxides: Allylation of Propargyl Alcohols
G. W. Kabalka, M.-L. Yao, S. Borella, J. Am. Chem. Soc., 2006, 128, 11320-11321.

Efficient Addition of Allylsilanes to α,β-Enones Using Catalytic Indium and Trimethylsilyl Chloride
P. H. Lee, D. Seomoon, S. Kim, K. Nagaiah, S. V. Damle, K. Lee, Synthesis, 2003, 2023-2026.

Stereoselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans Using an Intramolecular Allylation Strategy
P. J. Jervis, B. M. Kariuki, L. R. Cox, Org. Lett., 2006, 8, 4637-4640.

編譯自：organic chemistry portal