1080004-28-9Relevant academic research and scientific papers
Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G
Fairhurst, Nathan W. G.,Mahon, Mary F.,Munday, Rachel H.,Carbery, David R.
, p. 756 - 759 (2012/03/26)
The Ireland - Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
An Ireland-Claisen approach to β-alkoxy α-amino acids
Tellam, James P.,Kociok-Koehn, Gabriele,Carbery, David R.
supporting information; experimental part, p. 5199 - 5202 (2009/06/18)
(Chemical Equation Presented) A diastereoselective Ireland-Claisen approach to β-alkoxy α-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.
