134810-65-4

Upstream product

• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 140139-10-2 α-bromobenzyloxy(t-butyl)dimethylsilane 
• 74812-76-3 O-(tert-butyldimethylsilyl)propen-2-ol 
• 100-52-7 benzaldehyde 
• 340165-30-2 4-(tert-butyldimethylsilyloxy)-4-phenylbut-1-ene 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 140139-04-4 <α-(t-butyldimethylsilyloxy)benzyl>tributylstannane 

Relevant academic research and scientific papers

Discovery of a practical direct O2-coupled wacker oxidation with Pd[(-)-sparteine]Cl2

The discovery of a direct O2-coupled Wacker oxidation with use of balloon pressure of O2 and low catalyst loading is described. Use of (-)-sparteine as a ligand on Pd prevents olefin isomerization and leads to selective formation of methyl ketones from terminal olefins in good yields. Oxidation of enantiomerically enriched substrates is reported with no observed racemization.

Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions

Here, a palladium-catalyzed functionalization of unactivated sp3 C-H bonds with internal alcohol nucleophiles is described. Directed by an oxime-masked alcohol, annulation chemoselectively occurs at the β position, leading to a range of aliphatic cyclic ethers with four- to seven-membered rings. Tethered primary, secondary, and tertiary free hydroxyl groups can all react to give the corresponding cyclized products. In addition, benzyl and silyl protected alcohols can also be directly coupled. An sp3 C-H activation/intramolecular SN2 pathway was proposed.

Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans

An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.

QUINOLINE-OXAZOLINE COMPOUNDS AND THEIR USE IN OXIDATION SYNTHESIS

A quinoline-oxazoline compound having the formula: where one of X1 and X2 is N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula such that when X1 is N R2 is Z and R1 is absent, and when X2 is N either R1 or R3 is Z and R2 is absent. R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center. These compounds can be complexed with a suitable coordination center such as catalytically active palladium and can be highly useful in catalytically oxidizing alkenes with high regioselectivity.

Cross Aldol Products from α-Haloalkoxysilanes and Silyl Enol Ethers

α-Haloalkoxysilanes have been prepared by cleavage of the C-S bond in O,S-acetals with sulfuryl chloride, and by cleavage of C-Sn bond in α-silyloxystannanes by bromine.The α-haloalkoxysilanes, both after isolation or after preparation in situ react with silyl enol ethers to yield silyl-protected cross aldol products.The reaction is catalyzed by Lewis acids.

Reversal Phenomena of the Preferential Activation of Aldehydes to the Corresponding Acetals under Non-Basic Conditions. The Chemoselective Aldol Reaction of Aldehydes with t-Butyldimethylsilyl Enol Ethers Using TBSCl-InCl3 as a Catalyst

In the presence of a catalytic amount of t-butyldimethylsilyl chloride (TBSCl) and indium(III) chloride (InCl3), aldehydes smoothly react with t-butyldimethylsilyl enol ethers to afford the corresponding aldol adducts in good yields whereas acetals do not