953787-28-5Relevant academic research and scientific papers
Thio-Claisen rearrangement used in preparing anti-β-functionalized γ,δ-unsaturated amino acids: Scope and limitations
Liu, Zhihua,Mehta, Sukeshi J.,Lee, Kwang-Soo,Grossman, Bryan,Qu, Hongchang,Gu, Xuyuan,Nichol, Gary S.,Hruby, Victor J.
scheme or table, p. 1289 - 1300 (2012/04/10)
Multifunctionalized amino acids, especially amino acids with unsaturation, are important, demanding building blocks in peptide chemistry. Here we present a summary of our most recent study using the thio-Claisen rearrangement for the synthesis of anti-β-f
Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids
Qu, Hongchang,Gu, Xuyuan,Liu, Zhihua,Min, Byoung J.,Hruby, Victor J.
, p. 3997 - 4000 (2008/02/11)
Optically active anti-β-substituted γ,δ-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.
