Copper-Catalyzed Oxidative Self-Coupling of α-Amino Carbonyl Compounds for the Synthesis of Tetrasubstituted 1,4-Enediones

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2422-2426
Author(s):  
Bing Yi ◽  
Jiannan Xiang ◽  
Niannian Yi ◽  
Yi Xiong ◽  
Qingjun Huang ◽  
...  
Keyword(s):  
Double Bond ◽  
Carbonyl Compound ◽  
Carbonyl Compounds ◽  
Simultaneous Formation ◽  
High Stereoselectivity

A protocol for the copper-catalyzed oxidative self-coupling of α-amino carbonyl compounds has been developed for the synthesis of tetrasubstituted 1,4-enediones (Z-isomers) in moderate to good yields through the cleavage of four sp3C–H bonds and the simultaneous formation of one C=C double bond in the α-amino carbonyl compound. The strategy has the advantages of using readily available starting ­materials and of high stereoselectivity.

scholarly journals Broad scope gold(i)-catalysed polyenyne cyclisations for the formation of up to four carbon–carbon bonds

2017 ◽  
Vol 15 (10) ◽  
pp. 2163-2167 ◽  
Author(s):  
Zhouting Rong ◽  
Antonio M. Echavarren
Keyword(s):  
Single Step ◽  
Simultaneous Formation ◽  
Broad Scope ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
First Time ◽  
High Stereoselectivity

The polycyclisation of polyeneynes catalyzed by gold(i) has been extended for the first time to the simultaneous formation of up to four carbon–carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings.

Effets de solvant sur les complexes par transfert de charge iode – composés thiocarbonylés

1987 ◽  
Vol 65 (9) ◽  
pp. 2106-2108 ◽  
Author(s):  
Georges Guiheneuf ◽  
José-Luis M. Abboud ◽  
Widded Bouab
Keyword(s):  
Charge Transfer ◽  
Hydrogen Bonds ◽  
Carbonyl Compound ◽  
Carbonyl Compounds ◽  
The Other ◽  
Charge Transfer Complexes

The effects of solvents on different iodine – thiocarbonyl base charge-transfer complexes of variable stability have been examined and these are compared with the effects of solvents of the iodine – carbonyl compound complexes. There is an inversion of the effect of those solvents that can form hydrogen bonds on going from one series to the other, which is attributed to the fact that the carbonyl compounds are hard bases while the thiocarbonyl compounds are soft bases. [Journal translation]

Reduction of conjugate double bonds with trichlorosilane

2000 ◽  
Vol 78 (11) ◽  
pp. 1396-1398 ◽  
Author(s):  
Moni Chauhan ◽  
Philip Boudjouk
Keyword(s):  
Double Bond ◽  
Carbonyl Compounds ◽  
Double Bonds ◽  
Cyclic Ketones ◽  
Unsaturated Esters ◽  
Mild Conditions ◽  
Carbon Double Bond

A variety of α,β-unsaturated esters and cyclic ketones underwent smooth reduction of the carbon–carbon double bond with a combination of inexpensive and readily available trichlorosilane and CoCl2. The reactions are performed under very mild conditions and products are obtained in high yields.Key words: reduction, carbonyl compounds, trichlorosilane, ketones, chemoselectivity.

scholarly journals Evaluation of carbonyl emission from diesel engine generator using biodiesel fuel

2015 ◽  
Vol 18 (4) ◽  
pp. 179-191
Author(s):  
Hien Thi To ◽  
Khang Minh Tu ◽  
Vinh Xuan Le ◽  
Takenaka Norimichi
Keyword(s):  
Diesel Engine ◽  
Carbonyl Compound ◽  
Diesel Fuel ◽  
Carbonyl Compounds ◽  
Biodiesel Fuel ◽  
Particulate Matters

This research was carried out to measure and evaluate the emission of particulate matters and the emission of carbonyl compounds from diesel engine KAMA - KDE3500T generator under 1.5 kW load for seven test fuels: B0 (pure diesel fuel) B10 (10 % palm biodiesel + 90 % pure diesel fuel), B20, B30, B50, B75, and B100, respectively. The results showed that the emission concentration of particulate matters reduced from B0 to B20, and increased from B30 to B100. The concrete data were that 348.65 mg/m3, 297.27 mg/m3, 168.59 mg/m3, 169.74 mg/m3, 259.98 mg/m3, 330.30 mg/m3 and 522.98 mg/m3 for B0, B10, B20, B30, B50, B75 and B100, respectively. The emission concentration of carbonyl compound raised form B0 to B30, and suddenly decreased at B50, and increased again from B75 to B100. The concrete data were that 67.99 mg/m3, 87.35 mg/m3, 99.10 mg/m3, 100.96 mg/m3, 65.79 mg/m3, 102.32 mg/m3, 102.38 mg/m3 for B0, B10, B20, B30, B50, B75 and B100, respectively. The highest concentration compounds were formaldehyde, acetaldehyde, and acetone.

scholarly journals Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens)

2016 ◽  
Vol 11 (12) ◽  
pp. 1934578X1601101
Author(s):  
Miu Iijima ◽  
Hiromichi Kenmoku ◽  
Hironobu Takahashi ◽  
Jung-Bum Lee ◽  
Masao Toyota ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Metabolic Engineering ◽  
Double Bond ◽  
Carbonyl Compound ◽  
Catalytic Properties ◽  
Biotechnological Applications ◽  
Pelargonium Graveolens ◽  
Double Bond Reductase ◽  
Herbal Plant

Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPR1–3) have been cloned from P. graveolens, as possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into ( S)-citronellal in the presence of NADPH. Thus, the α,β-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs, as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β-unsaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic engineering, based on their catalytic properties, are discussed herein.

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