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New acyl(allyl)- and acyl(vinyl)silanes have been synthesized in order to explore cross metathesis or ring-closing metathesis as a new way towards bis(acyl)silanes or unsaturated cyclic acylsilanes, respectively. Metathesis from acylsilanes did not work but their precursors, in particular in...
Allylic ethers undergo insertions of silylenes into C–O bonds to form allylic silanes. Silylene insertion into C–O acetal bonds was also observed. Formation of silylene ylide intermediates led to (1,2)-Stevens rearrangement products as well as (2,3)-sigmatropic products depending upon the...
The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr 3 , and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr 3 /Me 3 SiBr are described. In both reaction systems, various types of silyl enolates were used to give...
Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete γ-selectivity. A further process of hetero-Diels–Alder cycloaddition, leading to chiral pyran-4-one...
The structures and charge distributions of substituted silenolates (H 2 SiC( O)X) − (X=H, SiH 3 , Me, t -Bu, OMe, NMe 2 ; group A ), (Y 2 SiC( O)H) − (Y=H, F, Me, Ph, SiH 3 , SiMe 3 ; group B ), and (Y 2 SiC( O)X) − (Y=Me, X= t -Bu, and Y=SiMe 3 ; X= t -Bu, OMe, NMe 2 ; group C ) were...
We describe a seven-step total synthesis of the triquinane sesquiterpene (±)-cameroonanol using a Lewis acid-promoted (3+2) cycloaddition of an allylsilane and a modified Fleming–Tamao oxidation as key reactions.
We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)oxy substituent. The transformations are best described mechanistically as intramolecular silatropic ene reactions based on stereoselectivity, kinetic and computed transition state data. The overall process...
We developed an efficient, practical, and robust method for stereoselective preparations of ( Z )-ketene trimethylsilyl (TMS) thioacetals from thioesters and alkyl (1 Z )- or (1 Z ,3 E )-1,3-bis(TMS)dienol ethers from alkyl β-ketoesters. The former preparation was performed by convenient...
The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6 , 15 yields indenone derivatives 11 , 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation ( 8 , 17 )....
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