P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System

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Title:P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System
Creators:
Drahoňovský, Dušan
Štěpnička, Petr
Dvořák, Dalimil
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 3, pp. 361-369
Uncontrolled Keywords:P-Chiral ligands, Oxazolines, Allylic substitutions, Palladium, Ferrocenes, Enantioselective catalysis

Abstract

P-Chiral (<i>S</i>,<i>R</i><sub>P</sub>)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (<strong>6</strong>) and (<i>S</i>,<i>S</i><sub>P</sub>)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (<strong>7</strong>) were prepared by the procedure developed by Jugé, starting from enantiomerically pure (-)- or (+)-ephedrine and dichloro(phenyl)phosphine. Compounds <strong>6</strong> and <strong>7</strong> were examined for asymmetric induction in the Pd-catalyzed reaction of <i>rac</i>-1,3-diphenylallyl acetate with dimethyl malonate. The best results were obtained with <strong>7</strong> (98% ee), while <strong>6</strong> gave 82% ee. <p>

Title:P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System
Creators:
Drahoňovský, Dušan
Štěpnička, Petr
Dvořák, Dalimil
Uncontrolled Keywords:P-Chiral ligands, Oxazolines, Allylic substitutions, Palladium, Ferrocenes, Enantioselective catalysis
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:70
Number:3
Page Range:pp. 361-369
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20050361UNSPECIFIED
ID Code:2365
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Drahoňovský, Dušan; Štěpnička, Petr; Dvořák, Dalimil (2005) P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System. Collection of Czechoslovak Chemical Communications, 70 (3). pp. 361-369. ISSN 0010-0765

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