171920-16-4Relevant academic research and scientific papers
The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling
Anderson, James C.,Anguille, Stephane,Bailey, Rosalyn
, p. 2018 - 2019 (2002)
A vinyl-phenylsilane has been used as a masked vinyl organometallic for a cross coupling reaction with phenyl iodide to provide the cine substitution product in high yield.
Diastereoselective acyclic aza-[2,3] Wittig sigmatropic rearrangements
Anderson, James C.,Smith, Stephen C.,Swarbrick, Martin E.
, p. 1517 - 1521 (2007/10/03)
The scope of anion-stabilising groups in promoting and controlling the diastereoselection of the aza-[2,3] Wittig sigmatropic rearrangement has been assessed by the syntheses of allylic amines 1c-g that have incorporated SiPhMe2, Ph, SPh, SOPh and SO2Ph respectively at the C-2 position. The subsequent anionic [2,3]-sigmatropic rearrangements are analysed with respect to the extent of diastereoselection of the product homoallylic amines 2 and 3. It appears that silicon not only is the most efficient at electronically facilitating this rearrangement, but its steric bulk controls the diastereoselectivity of the process exclusively. Phenyl and phenylthio substituents also have a similar, but decreased, effect on diastereoselection that mirrors their lower steric bulk in comparison to the silicon derivative. Sulfoxide and sulfone substituents are incompatible with the reaction conditions required for rearrangement.
Aza--Wittig Sigmatropic Rearrangement of Crotyl Amines
Anderson, James C.,Siddons, D. Craig,Smith, Stephen C.,Swarbrick, Martin E.
, p. 1835 - 1836 (2007/10/02)
The first example of an acyclic aza--Wittig sigmatropic rearrangement is presented, and its application to the synthesis of unnatural amino acids is described.
