Facile synthesis of phosphorus-containing heterocycles

Boyd, E. A.; Boyd, Mark; Kerrigan, Frank

doi:10.1016/0040-4039(96)01127-6

Cited by 17 publications

(9 citation statements)

References 6 publications

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“…To enable comparison of the asymmetric ligands with C 2 -symmetric analogues, the P,P - and N,N - ligands 7 and 8 were also synthesized. The former ligand ( 7 ) was obtained from reaction of ( S )- 24 with ammonium phosphinate (to give 25 , 42%), followed by reduction with phenylsilane to give 26 , isolated as its borane adduct (43%, Scheme ). Disubstitution of ethylene glycol ditosylate with 26 −BH 3 resulted in a low yield of product, and as this route can give access to only one diastereoisomer it was not considered useful.…”

Section: Resultsmentioning

confidence: 99%

Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions

et al. 2003

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Chiral P,N-ligands with pseudo-C2 and pseudo-Cs symmetry based on chiral pyrrolidine and phospholane rings or on dinaphthatodihydroazepino and dinaphthatodihydrophosphepino moieties were prepared and assessed in the palladium-catalyzed allylic substitutions of allylic acetates. Higher selectivity was achieved with pseudo-C2-symmetric ligands based on the binaphthyl skeleton than with the analogous C2-symmetric P,P- and N,N-analogues. Pseudo-C2-type ligands had properties superior to those of pseudo-meso-type ligands when 1,3-diphenyl-2-propenyl acetate was used as a substrate, whereas the reverse situation was found for 3-cyclohexenyl acetate. Chirally flexible ligands, prepared by substitution of one of the rigid binaphthyl skeletons for a flexible biphenyl system, were found to induce chirality to the same extent as a 1:1 mixture of the rigid ligands.

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Section: Resultsmentioning

confidence: 99%

Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions

et al. 2003

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“…Compound 2 was prepared from d -aspartate in six steps, protected as a benzyloxycarbonyl derivative and then converted to iodide 3 under previously reported conditions . Treatment of 3 with bis(trimethylsilyl)phosphonite under mild conditions (room temperature, CH 2 Cl 2 ) gave the d -Glu analogue 5 in 32% yield . The main side product in this reaction displayed MS and 1 H NMR data that were consistent with an amino acid containing a reduced propyl side chain.…”

mentioning

confidence: 93%

“…This strategy cannot be used with simple primary phosphinic acids such as the γ-phosphinic acid analogue of glutamate, 5 (note that the linkage of the MurE product is via the γ-carboxylate of d -Glu). While routes to the racemic phosphinic acid analogue of glutamate are known, we wished to prepare optically pure 5 , and since 2 could be used as a common precursor to both amino acid analogues, we chose to prepare 5 using Arbuzov-like chemistry …”

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confidence: 99%

A Phosphinate Inhibitor of the meso-Diaminopimelic Acid-Adding Enzyme (MurE) of Peptidoglycan Biosynthesis

et al. 1998

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“…These both contain asymmetrical centrally located oxo ligands, that is, the nonclassical forms which display C 2v symmetry. Reactions between VO(acac) 2 and diphenylphosphinic acid resulted an intractable substance analyzing as (VO(O 2 PPh 2 ) 2 ) ∞ , 3 , while reactions with 2-hydroxyisophosphindoline-2-oxide at room temperature in CH 2 Cl 2 affords ((H 2 O)VO(O 2 P( o- (CH 2 ) 2 (C 6 H 4 )) ∞ , 4 , and at 120 °C in EtOH yields (VO(O 2 P( o- (CH 2 ) 2 (C 6 H 4 )) ∞ , 5 . The crystal structures of 1 , a cocrystallized mixture consisting of 21.7(6)% 1 and 78.3(6)5% 2 and pure 2 , and the thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), room temperature magnetic susceptibility measurements on 1 – 5 and the variable temperature magnetic susceptibility measurements and low temperature magnetization measurements for complex 2 are described.…”

Section: Introductionmentioning

confidence: 99%

Syntheses, X-ray Structural Characterizations, and Thermal Stabilities of Two Nonclassical Trinuclear Vanadium(IV) Complexes, (V₃(μ₃-O)O₂)(μ₂-O₂P(CH₂C₆H₅)₂)₆(H₂O) and (V₃(μ₃-O)O₂)(μ₂-O₂P(CH₂C₆H₅)₂)₆(py), and Polymeric Complexes of Stoichiometry (VO(O₂PR₂)
Maass
¹
,
Chen
²
,
Zeller
³

et al. 2012
Inorg. Chem.
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The preparation and structural characterization of two trinuclear vanadium complexes, (V(3)(μ(3)-O)O(2))(μ(2)-O(2)P(CH(2)C(6)H(5))(2))(6)(H(2)O), 1, and (V(3)(μ(3)-O)O(2))(μ(2)-O(2)P(CH(2)C(6)H(5))(2))(6)(py), 2, are reported. In these nonclassical structures, the planar central core consists of the three vanadium atoms arranged in the form of an acute quasi-isosceles triangle with the central oxygen atom multiply bonded to the vanadium atom at the center of the vertex angle and weakly interacting with the two other vanadium atoms on the base sites, each of which contain one external multiply bonded oxygen atom. Reacting VO(acac)(2)in the presence of diphenylphosphinic acid affords (VO(O(2)PPh(2))(2))(∞), 3, while 2-hydroxyisophosphindoline-2-oxide at room temperature in CH(2)Cl(2) affords ((H(2)O)VO(O(2)Po-(CH(2))(2)C(6)H(4))(2))(∞), 4, and at 120 °C in EtOH yields (VO(O(2)P(o-(CH(2))(2)(C(6)H(4)))(∞), 5 on the basis of elemental analyses. The thermal and chemical stability of the complexes were assessed by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurements. The bond strengths of the vanadium atoms to the OH(2) ligand in 1 and to the NC(5)H(5) ligand in 2 were assessed at 10.7 and 42.0 kJ/mol respectively. Room temperature magnetic susceptibility measurements reveal magnetic moments for trinuclear 1 and 2 at 3.02(1) and 3.05(1) μ(B/mol), and also close to spin only values (1.73 μ(B)) values for 3, 4, and 5 at 1.77(2), 1.758(7), and 1.77(3) μ(B), respectively. Variable-temperature, solid-state magnetic susceptibility measurements were conducted on complex 2 in the temperature range of 2.0-298 K and at an applied field of 0.5 T. Magnetization measurements at 2 and 4 K confirmed a very weak magnetic interaction between the vanadyl centers.

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Facile synthesis of phosphorus-containing heterocycles

Cited by 17 publications

References 6 publications

Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions

Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions

A Phosphinate Inhibitor of the meso-Diaminopimelic Acid-Adding Enzyme (MurE) of Peptidoglycan Biosynthesis

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