423171-96-4

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 95932-32-4 tert-butyl (E)-cinnamyl carbonate 

Downstream Products

• 180295-27-6 3-Phenylpropanol triisopropyllsilyl ether 
• 122-97-4 3-Phenyl-1-propanol 

Relevant academic research and scientific papers

Diastereoselective borocyclopropanation of allylic ethers using a boromethylzinc carbenoid

A borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities. Several postfunction-alization reactions were also performed to illustrate the versatility of these building blocks.

Iridium-catalyzed enantioselective synthesis of allylic alcohols: Silanolates as hydroxide equivalents

(Chemical Equation Presented) Masked hydroxide: A highly regio- and enantioselective Ir-catalyzed allylic etherification of acyclic, achiral allylic carbonates can be achieved by using potassium silanolates as nucleophiles. The use of these hydroxide equi

Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN.

Unexpected deprotection of silyl and THP ethers induced by serious disparity in the quality of Pd/C catalysts and elucidation of the mechanism

Commercial Pd/C catalysts show different catalytic activity toward the deprotection of silyl and THP ethers. The Pd/C purchased from Merck and ACROS exhibits marked tendency to cleave these protective groups unexpectedly without hydrogen conditions although Aldrich's Pd/C (20,569-9) is inactive in the absence of hydrogen. It was proved that the Pd/C disparity toward the deprotection of TES and THP ethers results from residual acids and/or palladium chloride in the production process of Pd/Cs. Although a TES ether cleavage reaction in the absence of hydrogen and a THP ether cleavage reaction in the presence of hydrogen using 10% Pd/C were recently published, we could conclude they were only an acid-catalyzed solvolysis, the acid being released from the catalyst. Hydrogen is essential for the actual 10% Pd/C-catalyzed cleavage of TES ethers and THP ethers which must be stable under the true Pd/C-catalyzed hydrogenation conditions.