754178-74-0Relevant academic research and scientific papers
Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions
Miaskiewicz, Solène,Reed, John H.,Donets, Pavel A.,Oliveira, Caio C.,Cramer, Nicolai
supporting information, p. 4039 - 4042 (2018/03/13)
Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.
Development of biisoquinoline-based chiral diaminocarbene ligands: Enantioselective SN2′ allylic alkylation catalyzed by copper-carbene complexes
Seo, Hwimin,Hirsch-Weil, Dimitri,Abboud, Khalil A.,Hong, Sukwon
, p. 1983 - 1986 (2008/09/19)
Chiral biisoquinoline-based diaminocarbene ligands (BIQ) were designed to create a chiral environment extended toward the metal center, which was confirmed by an X-ray structure. The concise ligand synthesis is highlighted by a modified Bischler-Napieralski cyclization of bisamides prepared from readily available chiral phenethylamines, and allows easy variation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective SN2′ allylic alkylation with Grignard reagents showing SN2′ regioselectivity higher than 5:1 and enantioselectivity in the range of 68-77% ee.
Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes
Hunt, James C. A.,Lloyd, Cephas,Moody, Christopher J.,Slawin, Alexandra M. Z.,Takle, Andrew K.
, p. 3443 - 3454 (2007/10/03)
Addition of organolithium or Grignard reagents to (R)- or (S)-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride-diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N-O bond with zinc-acetic acid-ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77-100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-aminb alcohols 5. The Royal Society of Chemistry 1999.
