105857-62-3Relevant academic research and scientific papers
Stereoconvergent preparation of chiral vinylsilanes by cuprate substitution of α-acetoxyallylsilanes. Application to the synthesis of (S)-(+)-bishomomanicone
Guintchin, Boris,Bienz, Stefan
, p. 7527 - 7533 (2007/10/03)
Enantiomerically enriched (E)- and (Z)-configured α -acetoxyallylsilanes have been prepared starting from a chiral acylsilane bearing an asymmetric unit at the silicon portion. Treatment of these compounds with organocuprates afforded the respective vinylogous substitution products in high yields and high stereoselectivities. The transformations proceed essentially by complete anti attack of the nucleophiles to the allylic acetates and predominantly via transition states leading to the (E)-configured vinylsilane products. By the proper choice of the double bond geometry in the starting material, the configuration of the newly formed stereogenic center can be controlled. The method represents a new and flexible entry into chiral vinylsilanes that can be used for subsequent transformations. As an example, the α,β-unsaturated γ-chiral, naturally occurring ketone (S)-(+)-bishomomanicone was synthesized with this method, which represents the first synthetic access to this compound.
Application of modified Mosher's method for primary alcohols with a methyl group at C2 position.
Tsuda, Masashi,Toriyabe, Yuki,Endo, Tetsuya,Kobayashi, Jun'ichi
, p. 448 - 451 (2007/10/03)
The absolute configurations of a series of primary alcohols possessing a branched methyl group at C2 position were examined on the basis of a modified Mosher's method proposed by Minale et al. It was revealed that in many cases the absolute configurations
