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Stereoselective synthesis of dienyl phosphonates via extended tethered ring-closing metathesis

  • Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.

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Metadaten
Author:Bernd SchmidtORCiDGND, Oliver Kunz
DOI:https://doi.org/10.1021/ol4020078
ISSN:1523-7060 (print)
ISSN:1523-7052 (online)
Parent Title (English):Organic letters
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Volume:15
Issue:17
Pagenumber:4
First Page:4470
Last Page:4473
Funder:Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-3]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert