99808-99-8

Upstream product

• 56522-24-8 tert-butyldimethylsilyl cyanide 
• 100-52-7 benzaldehyde 
• 532-28-5 (RS)-mandelonitrile 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 151-50-8 potassium cyanide 
• 132868-67-8 (tert-butyldimethylsilyl)(phenyl)methanone 
• 2408-36-8 lithium cyanide 

Downstream Products

• 119788-51-1 (2R*,3S*)-2-Hydroxy-3-methyl-1-phenyl-1-pentanon 
• 119788-52-2 (2S*,3S*)-2-Hydroxy-3-methyl-1-phenyl-1-pentanon 
• 119788-75-9 (2R*,3S*)-2-(tert-Butyldimethylsilyloxy)-3-methyl-1-phenyl-1-pentanon 
• 119788-76-0 (2S*,3S*)-2-(tert-Butyldimethylsilyloxy)-3-methyl-1-phenyl-1-pentanon 
• 119788-59-9 (2S*,3S*)-2-(tert-Butyldimethylsilyloxy)-2,3-dimethyl-1-phenyl-1-pentanon 
• 119788-58-8 (2R*,3S*)-2-(tert-Butyldimethylsilyloxy)-2,3-dimethyl-1-phenyl-1-pentanon 
• 119788-61-3 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-1,3-diphenyl-butan-1-one 
• 119788-60-2 (2R*,3S*)-2-(tert-Butyldimethylsilyloxy)-2-methyl-1,3-diphenyl-1-butanon 
• 129687-05-4 1,2-anti-2-Amino-1-(t-butyl)dimethylsilyloxy-1-phenyl-4-pentene 
• 129687-05-4 1,2-syn-2-Amino-1-(t-butyl)dimethylsilyloxy-1-phenyl-4-pentene 
• 99809-03-7 2-(tert-butyldimethylsiloxy)-2-phenylthioacetamide 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 51096-49-2 2-benzylamino-1-phenyl-ethanol 
• 306961-72-8 Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-eth-(E)-ylidene]-amine 

Relevant academic research and scientific papers

Rapid additions of bulky tert-butyldimethylsilyl cyanide to hindered ketones promoted by heterogeneous tin ion-exchanged montmorillonite catalyst

Tin ion-exchanged montmorillonite (Sn-Mont) was found to be a powerful heterogeneous catalyst for the cyanosilylation of various ketones including congested ones with a bulky cyanide source, tert-butyldimethylsilyl cyanide (TBDMSCN), giving the corresponding cyanohydrin tert-butyldimethylsilyl ethers in good (85%) to excellent (>98%) yields at room temperature. Compared to the previously reported catalysts, Sn-Mont is easy to prepare, environmentally benign, nontoxic, noncorrosive, and recyclable.

Rhodium-catalyzed allylic substitution with an acyl anion equivalent: Stereospecific construction of acyclic quaternary carbon stereogenic centers

A highly regio- and stereospecific rhodium-catalyzed allylic alkylation of tertiary allylic alcohol derivatives with a cyanohydrin pronucleophile is described. This direct and operationally simple protocol provides a fundamentally novel approach toward the synthesis of α-quaternary substituted ketones and circumvents many of the inherent problems associated with conventional enolate alkylation reactions. The stereospecific variant of this reaction provides the enantiomerically enriched α-quaternary substituted allylic aryl ketone, which is a particularly challenging intermediate for more conventional enolate-based strategies.

Remarkable acceleration of cyanosilylation by the mesoporous Al-MCM-41 catalyst

The presence of the heterogeneous mesoporous Al-MCM-41 catalyst remarkably accelerated the cyanosilylation of various aldehydes and ketones with trialkylsilyl cyanide, giving the corresponding cyanohydrin silyl ethers in quantitative yields under mild reaction conditions. The Royal Society of Chemistry.

P(RNCH2CH2)N: Efficient catalysts for the cyanosilylation of aldehydes and ketones

The 1,2-addition of trialkylsilylcyanides to aldehydes and ketones produces the corresponding protected cyanohydrins in good to excellent yields when carried out at 0°C to room temperature in the presence of catalytic amounts of the nonionic strong base P(RNCH2CH2)N (R = Me, i-Pr) in THF. These catalysts are easily removed from the product by hydrolysis or column filtration through silica gel.

Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones

LiCl acts as a highly effective catalyst for cyanosilylation of various aldehydes and ketones to the corresponding silylated cyanohydrins. The reaction proceeds smoothly with a substrate/catalyst molar ratio of 100-100 000 at 20-25 °C under solvent-free conditions. α,β-Unsaturated aldehydes are completely converted to the 1,2-adducts. The cyanation products can be isolated by direct distillation of the reaction mixture.

Enantioselective synthesis of protected cyanohydrins

A straightforward process for the preparation of optically active protected cyanohydrins, important building blocks for the synthesis of drugs and agrochemicals, has been established. Lipase B from Candida Antarctica (CAL-B) catalysed the kinetic resoluti

1,2-Diphenylethylenediamine linked chiral Ti(IV) complex - A new entry to the highly enantioselective silylcyanation of aliphatic and aromatic aldehydes

Highly enantioselective silylcyanation of aliphatic and aromatic aldehydes was achieved by using a 1,2-diphenylethylenediamine linked chiral Ti(IV) complex as the catalyst.

Reaction of acylsilanes with potassium cyanide: Brook rearrangement under phase-transfer catalytic conditions

The reactions of acylsilanes with KCN under liquid-liquid phase-transfer catalytic conditions proceeded smoothly via the Brook rearrangement to produce O-silylated cyanohydrin derivatives in excellent yields. We also found that α-cyano carbanions generate

Reduction of α-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH): A Facile Preparation of α-Trialkylsiloxy Aldehydes and their Derivatives

The stepwise synthesis of α-trimethylsiloxy aldehydes and α-hydroxy aldehydes could be achieved via the reduction of α-trimethylsiloxy nitriles with diisobutylaluminium hydride (DIBAH) starting from a variety of ketones.The facile synthesis of optically active α-tert-butyldimethylsiloxy aldehydes was attained by combination of asymmetric silylcyanation of aldehydes and DIBAH reduction of optically active α-siloxy nitriles.Furthermore, in the reduction of some α-tert-butyldimethylsiloxy-β,γ-unsaturated nitriles, migration of the double bond took place to form more stable α-siloxy-α,β-unsaturated aldehydes under some reaction conditions.