88932-60-9

Upstream product

• 88932-59-6 2-(4-Methoxy-2-(trimethylsilyl)phenyl)-3,4,4-trimethyloxazolinium Iodide 
• 79606-43-2 N,N-diisopropyl-4-methoxybenzamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 75-77-4 chloro-trimethyl-silane 
• 123-11-5 4-methoxy-benzaldehyde 
• 88932-58-5 2-(4-Methoxy-2-(trimethylsilyl)phenyl)-4,4-dimethyl-2-oxazoline 

Downstream Products

• 134749-88-5 2-(4-methoxy-2-trimethylsilylphenyl)-1,3-dioxolane 
• 88932-61-0 1-(2-(Trimethylsilyl)-4-methoxyphenyl)-3-(trimethylsilyl)prop-1-ene 

Relevant academic research and scientific papers

Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes

A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.

Internal Lewis acid assisted benzoic acid catalysis

Internal Lewis acid assisted benzoic acid derivatives are introduced as new low-molecular-weight single-hydrogen-bond donor catalysts for the activation of nitroalkenes. Selected 2-borylbenzoic acid derivatives gave good yields of products in the addition of indoles to nitroalkenes. Control experiments suggest that both the internal Lewis acid coordination and the carboxylic acid functionalities are critical to the optimal performance of these catalysts. Georg Thieme Verlag Stuttgart New York.

Silicon-Mediated Synthesis of Bibenzyl Systems: Synthesis of Ring and Side-Chain Functionalized Hexestrol Derivatives

Derivatives of hexestrol , a non-steroidal estrogen, bearing photochemically reactive functional groups or γ-emmitting radionuclides, are useful as affinity labeling agents for the estrogen receptor or as imaging agents for receptor positive breast tumors, respectively.We have developed convenient synthetic routes to two side chain functionalized and aromatic ring functionalized hexestrol derivatives, based on a direct benzylic coupling reaction mediated by allylsilanes or silyl ketene acetals. 1-Dehydrohexestrol and variousaromatic ring substituted 1-dehydrohexestrol derivatives can be prepared by coupling 3-(trimethylsilyl)-1-(4-methoxyphenyl)propene with various reactive benzylic derivatives, and pentestrol derivatives are prepared by the coupling of the silyl ketene acetal derivative of p-methoxyphenyl acetic ester with benzylic derivatives.The R*,S* (erythro) and R*,R* (threo) diastereomers formed in each case can be separated readily by chromatography and recrystallization.This silicon-mediated approach to functionalized hexestrol derivatives provides a convenient route to many compounds of interest as biochemical probes and receptor-based diagnostic reagents.