Hosomi Sakurai反应是指在路易斯酸催化下各种亲电试剂和烯丙基三甲基硅烷反应进行烯丙基化的反应。此反应中Lewis酸是反应能够进行的关键。

反应机理

Note: 硅烷对β 碳正离子有稳定作用 (β effect)

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

A. Fürstner, D. Voigtländer, Synthesis, 2000, 959-969.

最新文献

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 Brønsted Acid Catalyst for Hosomi-Sakurai Reactions
M. Barbero, S. Bazzi, S. Cadamuro, S. Dughera, C. Piccinini, Synthesis, 2010, 315-319.

Efficient Brønsted 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.

A selective coupling of alkynylsilanes and allyltrimethylsilane is catalyzed by 5 mol% of indium tribromide under mild conditions to afford the corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in excellent yields.
J. S. Yadav, B. V. S. Reddy, M. Sridhar Reddy, G. Parimala, Synthesis, 2003, 2390-2394.

An enhanced Lewis acid system of InCl₃ and Me₃SiBr can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.
T. Saito, Y. Nishimoto, M. Yasuda, A. Baba, J. Org. Chem., 2006, 71, 8516-8522.

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.

编译自：organic chemistry portal