16980-55-5Relevant academic research and scientific papers
Influence of Alcohol β-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates
Graton, Jerome,Compain, Guillaume,Besseau, Francois,Bogdan, Elena,Watts, Joseph M.,Mtashobya, Lewis,Wang, Zhong,Weymouth-Wilson, Alex,Galland, Nicolas,Le Questel, Jean-Yves,Linclau, Bruno
supporting information, p. 2811 - 2819 (2017/03/05)
Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen-bond (H-bond) donat
Highly efficient conversion of alcohols to isocyanides
Kitano,Chiba,Tada
, p. 437 - 443 (2007/10/03)
Treatment of tertiary alcohols with silver salts (AgClO4, AgBF4, or AgOTf) and trimethylsilyl cyanide (TMSCN), followed by hydrolysis, directly affords excellent yields of corresponding isocyanides. This reaction proceeds selectively
Ligand effects on diastereoselective addition of organocerium reagents to aldehydes and cyclic ketones
Greeves, Nicholas,Lyford, Lisa,Elizabeth Pease
, p. 285 - 288 (2007/10/02)
A new class of chiral dialkoxy- and diaryloxyorganocerium reagent has been prepared and the diastereoselectivity of carbonyl addition reactions has been compared with that of conventional organocerium reagents.
Sterically Crowded Aryloxide Compounds of Aluminium: Hydrides and Homoleptic Aryloxides
Healy, Matthew D.,Mason, Mark R.,Gravelle, Philip W.,Bott, Simon G.,Barron, Andrew R.
, p. 441 - 454 (2007/10/02)
Interaction of and with HOR1 (R1 = C6H2But2-2,6-Me-4) allows for the isolation of 1)(NMe3)> 1 and 1)(NMe3)> 2 respectively.Compound 1 exists in both mono- and di-meric forms in the solid state.The reaction of 1 with NH2But results in ligand redistribution to give 1)2(NH2But)> 3.Similarly, multiple recrystallisation of 1 from Et2O allows for the isolation of 1)2(OEt2)> 4, while addition of HOR2 (R2 = C6H3Ph2-2,6) to 1 yields the mixed aryloxide complex 1)(OR2)(NMe3)> 5.Interaction of compound 1 with benzophenone results in the formation of the bridged dimer 1)(μ-OCHPh2)>2> 6.The reaction of 3 molar equivalents of HOR1 with LiAlH4 yields, in addition to 1)(OEt2)>2>, compound 4, which reacts further with H2O, HOR1 or NH2C6H2Cl3-2,4,6 to give 1)2>2> 7, 1)3> 8 or 1)2(NHC6H2Cl3-2,4,6)> 13 respectively.Compounds 8 and 13 form stable Lewis acid-base complexes 1)3L> t-4 12> and 1)2(NHC6H2Cl3-2,4,6)L> (L = Et2O 14, py 15 or 3,5-dimethylpyridine 16).The presence of a slow ligand exchange for compounds 9 and 12 was investigated by 1H NMR spectroscopy.The molecular structures of 1, 3, 4, 8 and 12 have been confirmed by X-ray crystallography.
Unprecedented Stereoselectivity in the Addition of Organoiron(II) Reagents to Cyclohaxanone Derivatives
Reetz, Manfred T.,Stanchev, Stephan
, p. 328 - 330 (2007/10/02)
Various organoiron(II) reagents undergo Grignard-type additions to substituted cyclohexanone derivatives, C-C bond formation occurring stereoselectively from the equatorial direction (97 - 100percent selectivity).
Ligand effects in selective carbonyl addition reactions of organomanganese and cerium reagents
Reetz, Manfred T.,Haning, Helmut,Stanchev, Stephan
, p. 6963 - 6966 (2007/10/02)
Transmetalation of organolithium reagents RLi (R = CH3, n-Bu) with manganese pivalate produces reagents of the type RMnOC(O)tBu which react stereoselectively with substituted cyclohexanones to afford the axial alcohols preferentially. These rea
Diastereoselective Addition of Organoytterbium Reagents to Carbonyl Substrates
Molander, Gary A.,Burkhardt, Elizabeth R.,Weinig, Peter
, p. 4990 - 4991 (2007/10/02)
Organoytterbium reagents, prepared by the addition of organolithiums or organomagnesiums to ytterbium(III) triflate, react in a highly diastereoselective fashion with a variety of chiral aldehydes and ketones.
Amphiphilic Reactions by Means of Exceptionally Bulky Organoaluminum Reagents. Rational Approach for Obtaining Unusual Equatorial, Anti-Cram, and 1,4 Selectivity in Carbonyl Alkylation
Maruoka, Keiji,Itoh, Takayuki,Sakurai, Minoru,Nonoshita, Katsumasa,Yamamoto, Hisashi
, p. 3588 - 3597 (2007/10/02)
Exceptionally bulky, oxygenophilic organoaluminum reagents, methylaluminum bis(2,6-di-tert-4-alkylphenoxide) (MAD and MAT), have been successfully utilized for stereoselective activation of carbonyl moiety.Combination of MAD or MAT with carbon nucleophiles such as organolithiums or Grignard reagents generates a new amphiphilic reaction system in which the alkylation may be interpreted as the nucleophilic addition of a reactive organometallic compound to an electrophilically activated carbonyl substrate in order to account for the regio- and stereochemical consequences.In contrast to the ordinary alkylations, the amphilic alkylation disclosed herein would be categorized into the new, yet unexplored class of alkylation that exhibits high chemoselectivity to carbonyl compounds, and more significantly it allows excellent equatorial and anti-Cram selectivity in carbonyl alkylations, hitherto difficult by the existing methodologies.Further, unusual conjugate addition of organolithium reagents to α,β-unsaturated carbonyl compounds has been accomplished by using the amphiphilic reaction system.
CH3Li/TiCl4: A NON-BASIC AND HIGHLY SELECTIVE GRIGNARD ANALOGUE
Reetz, M. T.,Kyung, S. H.,Huellmann, M.
, p. 2931 - 2935 (2007/10/02)
Treatment of CH3Li or CH3MgCl with TiCl4 results in quantitative formation of CH3TiCl3, a non-basic reagent which reacts chemo- and stereoselectively with carbonyl compounds.It is considerably more reactive than the alkoxy analogue CH3Ti(OCHMe2)3.This means that selective addition to ketones in the presence of such a functionality as nitro, cyano and ester groups is possible.Addition to enolizable ketones is smooth.The stereoselectivity is comparable to that observed for CH3Ti(OCHMe)3.
