60211-12-3Relevant academic research and scientific papers
PROCESS FOR PRODUCING HYDROXYMETHYL-ALCOHOLS
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Page/Page column 28, (2020/06/19)
The present invention relates to a process for producing an organic compound A, which comprises at least one primary alcoholic hydroxy group and at least one secondary alcoholic hydroxy group, comprising a process step, wherein a compound B, which comprises at least one nitrile group and at least one ketone group, is reacted with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.
Ruthenium-Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2-Amino Alcohols
Calleja, Pilar,Ernst, Martin,Hashmi, A. Stephen K.,Schaub, Thomas
supporting information, p. 9498 - 9503 (2019/04/30)
A new approach for the efficient and highly selective synthesis of 1,2-amino alcohols by direct reductive hydrolysis of N-formyl-protected α-amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed at 55 bar of H2, using a 6:1 mixture of 1,4-dioxane/water as solvent. In addition, hydroxymethyl alcohols were prepared from cyanoketones under very similar conditions.
Bent bonds (τ) and the antiperiplanar hypothesis, and the reactivity at the anomeric center in pyranosides
Parent, Jean-Fran?ois,Deslongchamps, Pierre
, p. 11183 - 11198 (2016/12/09)
The stereoselectivity of nucleophilic addition on oxocarbenium ions derived from the bicyclic pyranoside model with or without a C2-OR group can be understood through the use of the bent-bond and the antiperiplanar hypothesis in conjunction with the concept of hyperconjugation as an alternative interpretive model of structure and reactivity.
A general electron transfer reduction of lactones using SmI 2-H2O
Szostak, Michal,Collins, Karl D.,Fazakerley, Neal J.,Spain, Malcolm,Procter, David J.
supporting information; experimental part, p. 5820 - 5824 (2012/08/28)
Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI 2-H2O and a Lewis base to tune the redox properties of the complex. The current protocol permits instantaneous reduction of lactones to the corresponding diols in excellent yields, under mild reaction conditions and with useful chemoselectivity. We demonstrate the broad utility of this transformation through the reduction of complex lactones and sensitive drug-like molecules. Sequential electron transfer reactions and syntheses of deuterated diols are also described.
An unusual reaction of cyclic enol ethers with titanium(III) tetrahydroborate
Ravikumar,Chandrasekaran, Srinivasan
, p. 2973 - 2978 (2007/10/03)
Titanium(III) Tetrahydroborate formed in situ from titanium tetrachloride and benzyltriethylammonium tetrahydroborate (1:4) readily reacts with cyclic enol ethers in dichloromethane at -20°C to give the corresponding acyclic diols in high yields after simple aqueous work-up.
Stereocontrolled preparation of spirocyclic ethers by intramolecular trapping of oxonium ions with allylsilanes
Paquette, Leo A.,Tae, Jinsung
, p. 7860 - 7866 (2007/10/03)
The stereoselectivity of the spontaneous intramolecular cyclization of 2-(benzenesulfonyl)-2-(4-((trimethylsilyl)methyl)-4-pentenyl)tetrahydropyrans substituted by alkyl groups at various ring positions has been examined. For the 4- and 6-methyl derivatives, formation of the spirocyclic center occurs exclusively anti to the methyl. The outcome in the 5-methyl example is a 3.7:1 syn/ anti split. For the trans-4,6-dimethyl derivative, the substituents act in a reinforcing manner and direct cyclization uniquely in one direction. Both the cis and trans bicyclic ethers ring close on that π-surface of the intermediate oxonium ion syn to the angular hydrogen. The results are rationalized in terms of the predilection of the associated oxonium ions for nucleophilic capture via a chairlike or twist-boat transition state.
Synthetic and Stereochemical Studies of the Octahydro-1-benzopyran System
Griffiths, D. Vaughan,Wilcox, Geoffrey
, p. 431 - 436 (2007/10/02)
The cis and trans isomers of the octahydro-1-benzopyran system have been synthesised and their conformations studied by low-temperature (13)C and highfield (1)H n.m.r. spectroscopy.The position of the conformational equilibrium in the cis isomer at -70 deg C in CDCl3-CFCl3 (50:50) has been determined as approximately 99.5:0.5 (ΔG0 -8.9 kJ mol-1) in favour of the conformation having the oxygen axially disposed towards the cyclohexane ring.
PREPARATION OF 7-OXABICYCLONONANES AND 2-OXABICYCLODECANES SPECIFICALLY LABELLED WITH DEUTERIUM
Turecek, Frantisek
, p. 858 - 876 (2007/10/02)
trans-Annulated 7-oxabicyclononanes, labelled with deuterium at C(1), C(6), C(8) and C(9), and cis-annulated isomers labelled at C(1) and C(6) were prepared by cyclization of the cor
TRANSFORMATION OF ALLYLIC EPOXIDES TO TETRAHYDROFURFURYL ALCOHOLS VIA HYDROBORATION
Zaidlewicz, Marek,Sarnowski, Ryszard
, p. 281 - 284 (2007/10/02)
The allylic epoxides (1)-(4) were transformed to the tetrahydrofurfuryl alcohols (17)-(20), respectively.The formation of (6) and (10) in the hydroboration-oxidation of (4) is interpreted.The monohydroboration-oxidation of (13) and (14) gave (15) and (16), respectively.
