Neue Entwicklungen der Pauson-Khand-Reaktion

Geis, Oliver; Schmalz, Hans‐Günther

doi:10.1002/(sici)1521-3757(19980403)110:7<955::aid-ange955>3.0.co;2-t

Angewandte Chemie

1998

DOI: 10.1002/(sici)1521-3757(19980403)110:7<955::aid-ange955>3.0.co;2-t

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Neue Entwicklungen der Pauson-Khand-Reaktion

Oliver Geis

Hans‐Günther Schmalz

Abstract: Katalytische und asymmetische Varianten, Enone, Enine und Allene als weitere Edukte und zahlreiche Anwendungen in der Naturstoffsynthese belegen die Vielseitigkeit der Pauson‐Khand‐Reaktion [Gl. (a)], die inzwischen einen festen Platz in der organischen Synthese einnimmt.

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Cited by 63 publications

References 71 publications

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Evaluation of the Regioselectivity in Pauson-Khand Reactions of Substituted Norbornenes and Diazabicyclo[2.2.1]heptanes with Terminal Alkynes

Derdau

Laschat²,

Jones

2000

Eur. J. Org. Chem.

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1‐Methyl‐norbornene ester 9 and 1‐methyl‐2,3‐diazabicyclo[2.2.1]heptene ester 10 were employed in intermolecular Pauson‐Khand reactions with various terminal alkynes 11a‐f to give the dimethyl 1‐methyltricyclo[5.2.1.05,9]dec‐7‐en‐6‐one 2,3‐dicarboxylates 12 and 13, and diethyl 2,3‐diaza‐1‐methyltricyclo[5.2.1.05,9]dec‐7‐en‐6‐one 2,3‐dicarboxylates 14 and 15, respectively. Whereas the co‐cyclization of norbornene 9 with alkynes 11 bearing small substituents R resulted in the preferred formation of 12 (12:13 ≤ 85:15), regioisomer 13 was obtained as the major product when sterically bulky alkynes were employed (12:13 ≥ 6:94). For 2‐methyl‐3‐butyn‐2‐ol 11e a strong temperature dependency of the regioselectivity was found. The ratio of regioisomers (12e:13e) changed from 95:5 at ‐25 °C to 12:88 at 120 °C in toluene. In contrast, reactions with 2,3‐diazanorbornene 10 showed only moderate regioselectivities in favour of 14 (14:15 ≤ 69:31), regardless of the temperature and the size of R. The observed regioselectivities support a mechanism for the Pauson‐Khand reaction in which the apical rather than the basal anti oriented carbon monoxide ligand of cobalt alkyne complex 1 is replaced by the alkene.

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Evaluation of the Regioselectivity in Pauson-Khand Reactions of Substituted Norbornenes and Diazabicyclo[2.2.1]heptanes with Terminal Alkynes

Derdau

Laschat²,

Jones

2000

Eur. J. Org. Chem.

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Die Umwandlung von Titanacyclen in Carbocyclen: ein vorteilhafter Syntheseweg zu Cyclopentadienolen

1999

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Phosphane Sulfide/Octacarbonyldicobalt-Catalyzed Pauson – Khand Reaction Under an Atmospheric Pressure of Carbon Monoxide

Hayashi

Hashimoto²,

Yamamoto

et al. 2000

Angewandte Chemie

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Einen leichten Zugang zu Cyclopentenonen bieten katalytische, intra‐ und intermolekulare Pauson‐Khand‐Reaktionen in Gegenwart von Octacarbonyldicobalt und Tributylphosphansulfid (siehe Schema). Im Unterschied zu anderen Reaktionen dieses Typs verlaufen die hier beschriebenen unter milden Bedingungen (70 °C, 1 atm CO), und handelsübliches [Co2(CO)8] kann ohne weitere Reinigung als Katalysator verwendet werden.

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Neue Entwicklungen der Pauson-Khand-Reaktion

Abstract: Katalytische und asymmetische Varianten, Enone, Enine und Allene als weitere Edukte und zahlreiche Anwendungen in der Naturstoffsynthese belegen die Vielseitigkeit der Pauson‐Khand‐Reaktion [Gl. (a)], die inzwischen einen festen Platz in der organischen Synthese einnimmt.

Cited by 63 publications

References 71 publications

Evaluation of the Regioselectivity in Pauson-Khand Reactions of Substituted Norbornenes and Diazabicyclo[2.2.1]heptanes with Terminal Alkynes

Evaluation of the Regioselectivity in Pauson-Khand Reactions of Substituted Norbornenes and Diazabicyclo[2.2.1]heptanes with Terminal Alkynes

Die Umwandlung von Titanacyclen in Carbocyclen: ein vorteilhafter Syntheseweg zu Cyclopentadienolen

Phosphane Sulfide/Octacarbonyldicobalt-Catalyzed Pauson – Khand Reaction Under an Atmospheric Pressure of Carbon Monoxide

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