199277-70-8

Basic information

• Product Name: (S)-4-isopropyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole
• CAS NO: 199277-70-8
• Molecular Weight: 204.272
• Mol File: 199277-70-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S)-4-isopropyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-isopropyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole(199277-70-8)
• EPA Substance Registry System: (S)-4-isopropyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole(199277-70-8)

Safety Data

• Hazardous Substances Data: 199277-70-8(Hazardous Substances Data)

Upstream product

• 1620-75-3 2-Cyano-6-methylpyridine 
• 2026-48-4 (S)-valinol 
• 16369-05-4 valinol 
• 1343099-21-7 C₉H₁₂N₂O 
• 931-19-1 2-methylpyridine N-oxide 
• 109-06-8 α-picoline 
• 129821-92-7 methyl 6-methylpicolinimidate 

Downstream Products

• 2417528-13-1 (S)-2-(6-benzhydrylpyridin-2-yl)-4-isopropyl-4,5-dihydrooxazole 

Relevant articles and documents

Site-Selective Ni-Catalyzed Reductive Coupling of α-Haloboranes with Unactivated Olefins

A mild, chemo- and site-selective catalytic protocol that allows for incorporating an alkylboron fragment into unactivated olefins is described. The use of internal olefins enables C-C bond-formation at remote sp3 C-H sites, constituting a complementary and conceptually different approach to existing borylation techniques that are currently available at sp3 centers.

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**

A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.

Chemoselective oxidation of polyols with chiral palladium catalysts

Chiral palladium-based catalysts derived from pyridinyl oxazoline (pyOx) ligands catalyze the oxidation of alcohols, including 1,2-diols, triols, and tetraols, with high regio- and chemoselectivity. Screening of various chiral oxazoline-derived ligands for the oxidation of a model diol, 1,2-propanediol (1,2-PD), revealed that the nature of the ligand had a significant influence on the activity and chemoselectivity for oxidation of vicinal diols. The PyOx ligands containing an α-methyl substituent were the most active for the oxidation of 1,2-PD using benzoquinone as the terminal oxidant. Oxidation of vicinal diols and polyols occurs selectively at the secondary alcohol to afford α-hydroxy ketones in isolated yields of 62-87%. Chemoselective oxidation of meso-erythritol with the chiral [(S)-(α-Me(tert-Bu)PyOx)Pd(OAc)] 2[OTf]2 afforded (S)-erthyrulose in 62% yield and 24% ee.