ChemInform Abstract: Regioselective and Stereoselective 1,3-Dipolar Cycloadditions of Nitrile Oxide with Allylic Alcohols Prepared in situ from α,. beta.-Unsaturated Carbonyl Compounds with Grignard Reagents.

ChemInform ◽  
2010 ◽  
Vol 26 (36) ◽  
pp. no-no
Author(s):  
H. R. KIM ◽  
J. H. SONG ◽  
S. Y. RHIE ◽  
E. K. RYU
Keyword(s):  
Carbonyl Compounds ◽  
Nitrile Oxide ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Dipolar Cycloadditions

Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds

2000 ◽  
Vol 72 (9) ◽  
pp. 1715-1719 ◽  
Author(s):  
O. G. Kulinkovich
Keyword(s):  
Reaction Mechanism ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Unsaturated Compounds ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

Dialkoxytitanacyclopropane intermediates [or titanium (II)-olefin complexes] generated in situ from ethylmagnesium bromide and titanium (IV) isopropoxide react with allylic alcohols and allylic ethers to afford SN2' allylic ethylation products. The reaction proceeds with high regioselectivity and with low to high trans-/cis-stereoselectivity. This observation and others suggest a reaction mechanism involving an EtMgBr-initiated formation of titanacyclopentane ate complex 10 from titanacyclopropane-olefin complex 7 as a key step. Based on this assumption, a modified mechanism of titanium-mediated cyclopropanation of esters with Grignard reagents is proposed.

Cycloadditions of 2,5-dimethyl-3-furannitrile oxide to alkenes and alkynes

1990 ◽  
Vol 55 (10) ◽  
pp. 2481-2492 ◽  
Author(s):  
Eva Jedlovská ◽  
Lubor Fišera ◽  
Anna Balková ◽  
Jaroslav Kováč ◽  
Ladislav Štibrányi
Keyword(s):  
Mndo Method ◽  
Nitrile Oxide ◽  
Dipolar Cycloadditions

Regioselectivity of 1,3-dipolar cycloadditions of 2,5-dimethyl-3-furannitrile oxide (IIa) to alkenes or alkynes is described. Nitrile oxide IIa generated in situ reacts with monosubstituted alkenes or alkynes to give exclusively 5-substituted 3-(5-dimethyl-3 -furyl)-2-isoxazolines IV and isoxazoles V, 2,5-disubstituted alkenes sometimes afforded a mixture of regioisomeric isoxazolines. Reactivity of furannitrile oxides II and III in cycloadditions to ethene was studied by the MNDO method.

Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

2019 ◽  
Vol 17 (3) ◽  
pp. 622-638 ◽  
Author(s):  
Patrick G. McCaw ◽  
U. B. Rao Khandavilli ◽  
Simon E. Lawrence ◽  
Anita R. Maguire ◽  
Stuart G. Collins
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides

The generation of novel 1,2,5-oxathiazole-S-oxide cycloadducts from cycloaddition of nitrile oxide dipoles with α-oxo sulfines generated in situ from α-diazosulfoxides is reported.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Synthesis ◽  
2021 ◽  
Author(s):  
Santanu Ghora ◽  
Chinnabattigalla Sreenivasulu ◽  
Gedu Satyanarayana
Keyword(s):  
Functional Group ◽  
Exchange Process ◽  
Palladium Catalysis ◽  
Allylic Alcohols ◽  
Heck Coupling ◽  
One Pot ◽  
Synthetic Process ◽  
Intramolecular Condensation ◽  
The One

AbstractAn efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Formation of α,β-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols

1994 ◽  
Vol 35 (38) ◽  
pp. 7097-7098 ◽  
Author(s):  
Enrique Gómez-Bengoa ◽  
Pedro Noheda ◽  
Antonio M. Echavarren
Keyword(s):  
Carbonyl Compounds ◽  
Allylic Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation
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