Regio- and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo-Pauson-Khand Cyclization

Doing the two step: A very simple two‐step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson–Khand reaction, and can be used with a variety of bromoalkenes. Moreover, the final quench...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-01, Vol.51 (1), p.183-186
Main Authors: Barluenga, José, Álvarez-Fernández, Ana, Suárez-Sobrino, Ángel L., Tomás, Miguel
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Alkynes - chemistry
carbenes
chromium
Chromium - chemistry
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
enantioselectivity
Methane - analogs & derivatives
Methane - chemistry
Stereoisomerism
tungsten
Tungsten - chemistry
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Summary:Doing the two step: A very simple two‐step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson–Khand reaction, and can be used with a variety of bromoalkenes. Moreover, the final quenching allows the installation of reactive electrophiles (E). The enantiopure product cyclopentenones can be synthesized with an all‐carbon‐substituted quaternary stereocenter.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105362