107994-76-3Relevant academic research and scientific papers
Stereoselective synthesis of (Z)- and (E)-allylic silanes by copper- mediated substitution reactions of allylic carbamates with grignard reagents
Smitrovich, Jacqueline H.,Woerpel
, p. 1601 - 1614 (2007/10/03)
Both (Z)- and (E)-allylic silanes were prepared with high stereoselectivity by the copper-mediated substitution of allylic carbamates by organometallic reagents. The reaction of alkylmagnesium reagents with (E)- allylic carbamates provides (Z)-allylic silanes, whereas both alkylmagnesium and alkyllithium reagents react with (Z)-allylic carbamates to afford (E)- allylic silanes. Because Grignard reagents are often more facile to prepare than alkyllithium species, these reagents are the optimal nucleophiles for the synthesis of both (Z)- and (E)-allylic silanes. This method also allows readily available nonracemic allylic carbamates to be converted to chiral, nonracemic (Z)- and (E)-allylic silanes with high stereoselectivity.
The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes
Fleming, Ian,Lawrence, Nicholas J.
, p. 3309 - 3326 (2007/10/02)
The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron
ORGANIC SYNTHESIS WITH REAGENTS DERIVED FROM 3R3SiMgMe AND MnCl2
Fugami, Keigo,Hibino, Jun-ichi,Nakatsukasa, Shigeki,Matsubara, Seijiro,Oshima, Koichiro,et al.
, p. 4277 - 4292 (2007/10/02)
Synthetically useful reactions mediated by reagents derived from 3 equiv. of R3SiMgMe and MnCl2 are disclosed. (1) The manganese species reacted with terminal acetylenes to give 1,2-disilylated 1-alkenes.Mono- and bis(trimethylsilyl)acetylenes gave tri- a
SILYLMANGANATION OF 1,3-DIENES. A FACILE SYNTHESIS OF FUNCTIONALIZED VINYLSILANES
Fugami, Keigo,Nakatsukasa, Shigeki,Oshima, Koichiro,Utimoto, Kiitiro,Nozaki, Hitosi
, p. 869 - 870 (2007/10/02)
Treatment of 1,3-dienes with (R3Si)3 MnMgMe provides silylated allylmanganese compounds which add to carbonyl moiety with high regioselectivity.
