193546-34-8Relevant academic research and scientific papers
LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS
-
Page/Page column 146, (2015/10/05)
The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.
Total synthesis and stereochemistry assignment of 15-membered peptide alkaloids abyssenine B and mucronine E
Wang, Jing,Schaeffler, Lutz,He, Gang,Ma, Dawei
, p. 6717 - 6721 (2008/02/13)
The total synthesis of 15-membered peptide alkaloids abyssenine B and mucronine E was accomplished via olefination of phenylalanine-embodied aldehydes followed by CuI/N,N-dimethylglycine-catalyzed coupling of vinyl iodides with amides and FDPP-mediated ma
Synthesis of chirally pure 2,5-disubstituted diketopiperazines derived from trisubstituted phenylalanines
Danthi, Satyavijayan Narasimhan,Hill, Ronald A.
, p. 835 - 844 (2007/10/03)
Some new chirally pure 2,5-substituted diketopiperazines were synthesized starting from 2-methoxybenzyl alcohol. This multistep synthesis proceeds through the enzymatic synthesis of chirally pure amino acids, protection and dipeptide coupling, cyclization of dipeptide ester formates, and nitration of the resulting diketopiperazines.
