494205-61-7

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 2344-80-1 Chloromethyltrimethylsilane 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 

Downstream Products

• 402718-38-1 di[4-(1-trimethylsilanylmethyl-vinyl)phenyl]dimethylsilane 
• 494205-62-8 C₂₃H₃₄O₂Si₂ 
• 445399-06-4 4-[4-({1-[(trimethylsilyl)methyl]ethenyl}phenyl)dimethylsilyl]benzaldehyde 
• 122948-53-2 [2-(4-bromophenyl)prop-2-enyl]trimethylsilane 

Relevant academic research and scientific papers

Asymmetric synthesis of chiral polymers by means of repetitive addition of allylsilane to aldehyde

Monomers having both allyltrimethylsilyl and formyl groups were prepared. Chiral (acyloxy)borane initiated the repetitive polyaddition of the monomers to give optically active polymers having main chain configurational chirality. Optical purity of the chiral polymer was evaluated by the analysis of the degradation product.

Asymmetric polymer synthesis by repetitive Sakurai-Hosomi allylation reaction of compounds possessing both formyl and allylsilane functions

Trialkylallylsilanes generally react with aldehydes in the presence of a Lewis acid to the corresponding homoallylic alcohols. Chiral Lewis acids promote the same reaction to yield the enantiomerically-enriched homoallylalcohols. We have prepared four compounds (7-10) that possess both formyl and allylsilane functions. Lewis acids initiated self-polyaddition reactions of these compounds by means of repetitive allylation. The use of chiral Lewis acids resulted in the formation of optically active polymers that possess exo-methylene and secondary OH functions in their main chain. The optical purity of these chiral polymers was estimated based on the results of model asymmetric reactions between benzaldehyde and β-substituted allylsilanes and by controlled degradation.

Asymmetric allylation polymerization of bis(allylsilane) and dialdehyde containing Si-phenyl linkage

Repetitive Sakurai-Hosomi allylation between dialdehyde and bis(allylsilane) yielded a polymer having stereogenic carbons in its main chain. In the presence of an enantiopure Lewis acid catalyst such as chiral (acyloxy)borane (CAB), the allylation polymerization proceeded in a stereoselective manner to give optically active polymers. We have prepared new monomers containing Si-phenyl linkages for the asymmetric allylation polymerization. After polymerization, the Si-phenyl linkages in the main chain could be cleaved easily to give the corresponding chiral homoallylic alcohol. The enantiomeric purity of the chiral polymer was then evaluated by chiral HPLC analysis of the alcohol obtained from the degradation.