929208-40-2Relevant academic research and scientific papers
Stereoselective synthesis of 1,2,3-triol derivatives from α,β-unsaturated acylsilanes
Honda, Mitsunori,Nakamura, Takayoshi,Sumigawa, Takumi,Kunimoto, Ko-Ki,Segi, Masahito
, p. 565 - 577 (2014)
The stereoselective synthesis of 1,2,3- triol derivatives having contiguous stereogenic centers from α,β-unsaturated acylsilanes 1 was described. The oxidation of an olefin moiety of 1 with osmium tetroxide proceeded smoothly to give the corresponding 2,3- syn-dihydroxyacylsilanes 2. The protection of two hydroxy groups of 2 followed by a nucleophilic reaction to the silyl carbonyl group gave the corresponding silylated triol derivatives (7 and 8) with high stereoselectivity, depending on the kind of nucleophilic reagents. The deprotection for 7 and 8 and the following protodesilylation gave two isomers of possible four 1,2,3- triol derivatives. The stereoselective triol synthesis by asymmetric diolization of α-silylated allyl alcohols 11 derived by nucleophilic addition to 1 was also investigated.
Stereocontrolled construction of seven-membered carbocycles using a combination of Brook rearrangement-mediated [3 + 4] annulation and epoxysilane rearrangement
Nakai, Yoshio,Kawahata, Masatoshi,Yamaguchi, Kentaro,Takeda, Kei
, p. 1379 - 1387 (2007/10/03)
(Chemical Equation Presented) Reactions of Δ-silyl-γ,Δ- epoxy-α,β-unsaturated acylsilane with alkenyl methyl ketone enolate afford highly functionalized cycloheptenone derivatives via a tandem sequence featuring the combination of Brook rearrangement-medi
Mechanistic studies of the allylic rearrangements of α-silyloxy allylic silanes to silyloxy vinylic silanes
Kim, Angie I.,Kimmel, Kyle L.,Romero, Antonio,Smitrovich, Jacqueline H.,Woerpel
, p. 6595 - 6598 (2008/02/10)
(Chemical Equation Presented) Mechanistic evidence suggests that the Lewis acid-promoted allylic rearrangement of α-silyloxy allylic silanes proceeds along an ionic reaction pathway involving a contact ion pair. The driving force for this transformation i
