An Alternative Approach to Chiral 2-[1'-(Diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles

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Title:An Alternative Approach to Chiral 2-[1'-(Diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles
Creators:
Drahoňovský, Dušan
Císařová, Ivana
Štěpnička, Petr
Dvořáková, Hana
Maloň, Petr
Dvořák, Dalimil
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 4, pp. 588-604
Uncontrolled Keywords:<i>P</i>-Ligands, Oxazolines, Ferrocenes, Phosphines, Crystal structure, Enantioselective catalysis, Palladium

Abstract

The reaction of 1'-(diphenylphosphanoyl)ferrocenecarbonyl chloride, generated <i>in situ</i> by the reaction of 1'-(diphenylphosphanoyl)ferrocenecarboxylic acid and oxalyl chloride, with chiral aminoalcohols gave amidoalcohols [Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>P(O)Ph<sub>2</sub>)(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>C(O)NHCHRCH<sub>2</sub>OH)] <strong>13</strong>, (R&nbsp;= i-Pr, (<i>S</i>); R = i-Pr, (<i>R</i>); R = <i>t</i>-Bu, (<i>S</i>) and R = Ph, (<i>R</i>). The amidoalcohols <strong>13</strong> were converted to 2-[1'-(diphenylphosphanoyl)ferrocen-1-yl]-4,5-dihydrooxazoles <strong>14</strong> by ring-closing reaction with a tosyl chloride-triethylamine mixture. Subsequent reduction of <strong>14</strong> with trichlorosilane in the presence of triethylamine afforded the corresponding 2-[1'-(diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles <strong>10</strong>. Compounds <strong>13d</strong>, <strong>14d</strong> and <strong>10d</strong> were subjected to a detailed <sup>1</sup>H, <sup>13</sup>C and <sup>31</sup>P NMR analyses. CD spectra of all <strong>10</strong> were measured. <i>trans</i>-Dichlorobis{(<i>S</i>)-2-[1'-(diphenylphosphanyl)ferrocenyl]-4-isopropyl-4-5-dihydrooxazole-κ<i>P</i>}palladium(II) (<strong>15</strong>) was synthesised and its solid-state structure was determined by single-crystal X-ray diffraction. <p>

Title:An Alternative Approach to Chiral 2-[1'-(Diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles
Creators:
Drahoňovský, Dušan
Císařová, Ivana
Štěpnička, Petr
Dvořáková, Hana
Maloň, Petr
Dvořák, Dalimil
Uncontrolled Keywords:<i>P</i>-Ligands, Oxazolines, Ferrocenes, Phosphines, Crystal structure, Enantioselective catalysis, Palladium
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:4
Page Range:pp. 588-604
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010588UNSPECIFIED
ID Code:1813
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Drahoňovský, Dušan; Císařová, Ivana; Štěpnička, Petr; Dvořáková, Hana; Maloň, Petr; Dvořák, Dalimil (2001) An Alternative Approach to Chiral 2-[1'-(Diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles. Collection of Czechoslovak Chemical Communications, 66 (4). pp. 588-604. ISSN 0010-0765

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