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Synthesis of Unsaturated Nine-Membered Ring Ethers (Δ^3-Oxonenes) Containing a Z- or E-Configurated Double Bond: Thermodynamic versus Kinetic Control in Palladium-Catalyzed Allylic Cyclizations

Pohlmann, Jens and Sabater, Christopher and Hoffmann, H. M. R. (1998) Synthesis of Unsaturated Nine-Membered Ring Ethers (Δ^3-Oxonenes) Containing a Z- or E-Configurated Double Bond: Thermodynamic versus Kinetic Control in Palladium-Catalyzed Allylic Cyclizations. Angewandte Chemie International Edition, 37 (5). pp. 633-635. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20180508-084507122

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Abstract

Double stereocontrol is achieved in the Pd‐catalyzed cyclization of Δ^3‐oxonene precursors (see reactions outlined below). The configuration of the olefinic double bond and of the allylic carbon center α to the ether oxygen atom is dictated by the configuration of the double bond in the starting compound (E/Z), the Pd ligand (dppe = Ph_2PCH_2CH_2PPh_2), and the reaction time.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/(SICI)1521-3773(19980316)37:5<633::AID-ANIE633>3.0.CO;2-8DOIArticle
Additional Information:© 1998 Wiley‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany. Issue Online: 17 December 1998; Version of Record online: 17 December 1998; Manuscript received: 19 September 1998. This work was supported by the Fonds der Chemischen Industrie (PhD fellowships for J. P. and C. S.) and the Deutsche Forschungsgemeinschaft. We thank Dr. R. Wartchow, Institut für Anorganische Chemie der Universität Hannover, for the X-ray crystal structure analysis and Dr. J. M. Goodman, University of Cambridge, for calculations, and Degussa for a gift of palladium salts.
Funders:
Funding AgencyGrant Number
Fonds der Chemischen IndustrieUNSPECIFIED
Deutsche Forschungsgemeinschaft (DFG)UNSPECIFIED
Subject Keywords:Allyl complexes; Cyclizations; Medium‐sized rings; Palladium
Issue or Number:5
Record Number:CaltechAUTHORS:20180508-084507122
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180508-084507122
Official Citation:Pohlmann, J. , Sabater, C. and Hoffmann, H. M. (1998), Synthesis of Unsaturated Nine‐Membered Ring Ethers (Δ3‐Oxonenes) Containing a Z‐ or E‐Configurated Double Bond: Thermodynamic versus Kinetic Control in Palladium‐Catalyzed Allylic Cyclizations. Angewandte Chemie International Edition, 37: 633-635. doi:10.1002/(SICI)1521-3773(19980316)37:5<633::AID-ANIE633>3.0.CO;2-8
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86272
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:08 May 2018 16:00
Last Modified:03 Oct 2019 19:41

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