320618-65-3Relevant academic research and scientific papers
Stereocontrolled synthesis of (2S*,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement
Anderson, James C.,Flaherty, Alice
, p. 267 - 269 (2001)
Racemic synthesis of the non-proteinogenic amino acid (2S,3R,4R)-4-hydroxy-3-methylproline was discussed. Iodolactonization of an unstarurated amino acid derivative was done. Results showed that the silicon assisted aza-[2,3]-Wittig sigmatropic rearrangem
Hydrosilylation of alkynes catalyzed by ruthenium carbene complexes
Maifeld, Sarah V.,Tran, Michael N.,Lee, Daesung
, p. 105 - 108 (2007/10/03)
Hydrosilylation of terminal alkynes with a variety of silanes catalyzed by Cl2(PCy3)2RuCHPh (1) affords mainly the Z-isomer via trans addition in excellent yields. The presence of a hydroxyl group in close proximity to the
The aza-[2,3]-Wittig sigmatropic rearrangement of acyclic amines: Scope and limitations of silicon assistance
Anderson,Flaherty,Swarbrick
, p. 9152 - 9156 (2007/10/03)
The inclusion of a C-2 trialkylsilyl substituent into allylic amine precursors allows the base-induced aza-[2,3]-Wittig sigmatropic rearrangement to proceed in excellent yield and diastereoselectivity. The rearrangement precursors require a carbonyl-based nitrogen protecting group that must be stable to excess of strong base required for the reaction. The N-Boc and N-benzoyl group are very good at stabilizing the product anion and initiating deprotonation. The migrating groups (G) need to stabilize the intial anion by resonance and require G-CH3 pKa > 22 in order for the initial anion to be reactive enough for rearrangement. Products 7, 29b-d,f,g, and 23 are formed with high (10-20:1) anti diastereoselectivity. Product 23 containing the morpholine amide group is useful for preparing other carbonyl derivatives.
