852049-33-3Relevant academic research and scientific papers
Enantioselective γ-C(sp3)-H activation of alkyl amines via Pd(II)/Pd(0) catalysis
Shao, Qian,Wu, Qing-Feng,He, Jian,Yu, Jin-Quan
supporting information, p. 5322 - 5325 (2018/05/03)
Pd(II)-catalyzed enantioselective γ-C(sp3)-H cross-coupling of alkyl amines via desymmetrization and kinetic resolution has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands (APAO). A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners. The chiral γ-arylated alkylamine products are further transformed into chiral 2-substituted 1,2,3,4-tetra-hydroquinolines and spiro-pyrrolidines as important structural motifs in natural products and biologically active molecules.
Synthesis of amine functionalized oxazolines with applications in asymmetric catalysis
Miller, Jeremie J.,Rajaram, Sridhar,Pfaffenroth, Cornelia,Sigman, Matthew S.
experimental part, p. 3110 - 3119 (2009/09/05)
This paper describes the synthesis of three classes of amine functionalized oxazolines that have been successfully used in asymmetric catalysis in our laboratory. Failed synthetic routes and significantly improved procedures are discussed including the synthesis of ligands for Nozaki-Hiyama-Kishi (NHK) carbonyl allylation reactions that do not require chromatography for purification.
Modular syntheses of oxazolinylamine ligands and characterization of group 10 metal complexes
Caputo, Christine A.,Carneiro, Florentino D S.,Jennings, Michael C.,Jones, Nathan D.
, p. 85 - 95 (2008/02/12)
The syntheses of aminoalkyloxazoline and pyrrolidinyloxazoline ligands, each of which bear a pair of chiral centres, by both known and new routes are reported. Variable temperature NMR studies show that the known stepwise syntheses of the pyrrolidinyl compounds are not complicated by epimerization; however, coordination of one of the aminoalkyl derivatives to Pt(II) under conditions of prolonged heating to 80°C does give mixtures of diastereomeric N,N′-chelated complexes that result from inversion of the chiral centre associated with the aminoalkyl fragment. A new synthesis of pyrrolidinyloxazoline ligands that involves the Zn-catalyzed cyclization of Cbz-protected 2-cyanopyrrolidine and β-amino alcohols is also reported. This procedure offers the advantages of economy, shorter time, and fewer purification steps over the previously reported synthesis. In addition, the crystal structure of an enantiopure Pd(II) complex of an N.N′-chelated pyrrolidinyloxazoline is disclosed. This compound has a pseudo-C2 axis of symmetry, which may make it suitable for asymmetric catalytic applications.
Stereochemical diversity in chiral ligand design: Discovery and optimization of catalysts for the enantioselective addition of allylic halides to aldehydes
Lee, Jae-Young,Miller, Jeremie J.,Hamilton, Steven S.,Sigman, Matthew S.
, p. 1837 - 1839 (2007/10/03)
(Chemical Equation Presented) We have identified a new set of stereochemically diverse oxazoline ligands derived from simple amino acids that promote the Cr-catalyzed enantioselective addition of allylic halides to aldehydes in up to 95% ee. The Cr-cataly
