71787-56-9Relevant academic research and scientific papers
Ceric(IV) ammonium nitrate: A novel reagent for the synthesis of homoallyl alcohols
Yadav,Reddy,Krishna,Sadasiv,Chary, Ch. Janardhana
, p. 248 - 249 (2003)
A rapid and highly efficient method has been developed for the allylation of aldehydes with allyltributylstannane using a catalytic amount of eerie ammonium nitrate in acetonitrile under mild and neutral conditions to afford the corresponding homoallyl al
Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds
Reetz, Manfred T.,Haning, Helmut
, p. 117 - 120 (2007/10/03)
The reaction of the allyl indium sesquibromide (CH2 =CHCH2)3In2Br3 with four equivalents of a bulky lithium alkoxide ((CH3)3COLi or (CH3)3CCH2OLi) results in modified reagents which show unusual degrees of chemo-and stereoselectivity in reactions with carbonyl compounds. For example, in reactions with cyclohexanone derivatives, 84-93% equatorial attack with preferential formation of the axial alcohols is observed. Chiral aldehydes react in a highly diastereoselective manner.
Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions
Negri, Joanna T.,Paquette, Leo A.
, p. 8835 - 8841 (2007/10/02)
The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a domi
Stereoselective Addition of Organotitanium Reagents to Carbonyl Compounds
Reetz, Manfred T.,Steinbach, Rainer,Westermann, Juergen,Peter, Roland,Wenderoth, Bernd
, p. 1441 - 1454 (2007/10/02)
Titanation of alkyllithium or -magnesium compounds using ClTi(OR)3 results in reagents which show markedly increased diastereofacial selectivity (80 - 90percent) in reactions with α-chiral aldehydes or ketones.Titanation is also the method of choice in Grignard-type additions to substituted cyclohexanones; CH3Ti(OCHMe2)3 (6a) adds predominantly from the equatorial direction, while allyltitanium reagents 11b and 12 show axial preference.Crotyltitanium compounds react with carbonyl compounds to afford primarily adducts having anti-configuration, a process which is of particular value in case of ketones (anti/syn ratios up to 99:1).Titanation of (trimethylsilyl)allyllithium (48) with Ti(OCHMe2)4 reverses regioselectivity in reactions with aldehydes and ketones, β-hydroxy silanes 50 being the only observed products.These have anti-configuration and can be converted either into Z- or E-dienes using the Peterson elimination under basic or acidic conditions, respectively.
