- Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents
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Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.
- Chen, Jyun-Siao,Huang, Po-Hsun,Hsieh, Ya-Chi,Liu, Jen-Wei,Hsu, Hsiao-Lin,Zhang, Kai-Min,Wu, Ren-Tsung,Chang, Ting-Shuo,Liu, Yu-Hao,Wu, Hsin-Ru,Luo, Shun-Yuan
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supporting information
p. 754 - 762
(2021/12/02)
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- Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols
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One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).
- Casnati, Alessandra,Lichosyt, Dawid,Lainer, Bruno,Veth, Lukas,Dydio, Pawe?
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supporting information
p. 3502 - 3506
(2021/05/10)
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- Trimethylsilylazide: A Highly Reactive Silylating Agent for Primary and Secondary Alcohols
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Trimethylsilylazide reacts very rapidly with primary and secondary alcohols at room temperature to give high yields of trimethylsilyl ethers.
- Sinou, D.,Emziane, M.
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p. 1045 - 1046
(2007/10/02)
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- Generation of Metal-Free Silyl Anions from Disilanes and Fluoride Catalyst. Synthetic Reactions with Aldehydes and 1,3-Dienes
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The Si-Si bond of disilanes is found to be cleaved by tetrabutylammonium fluoride (TBAF) in hexamethylphosphoric triamide to produce metal-free silylanion and triorganosilyl fluoride.The disilane/TBAF reagent was studied spectrometrically.Sythetic application of the reagent with a catalytic amount of TBAF is illustrated by the reaction with aldehydes and 1,3-dienes.
- Hiyama, Tamejiro,Obayashi, Michio,Mori, Ichiro,Nozaki, Hitosi
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p. 912 - 914
(2007/10/02)
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