Stereo controlled synthesis of (E,Z)-dienals via tandem Rh(I) catalyzed propargyl claisen rearrangement

US9758499B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-9758499-B2
Application numberUS-201715398094-A
CountryUS
Kind codeB2
Filing dateJan 4, 2017
Priority dateJun 12, 2014
Publication dateSep 12, 2017
Grant dateSep 12, 2017

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Abstract

Official abstract text for this publication.

A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetallation step giving an (E,Z)-dienal. The reaction may be represented by the following sequence.

First claim

Opening claim text (preview).

What is claimed is: 1. A method to synthesize an (E,Z)-dienal compound having structure (V), the method comprising: contacting a compound having structure (IV) with a catalyst comprising Rh(I) to thereby prepare the compound having structure (V); wherein the compounds having structures (IV) and (V) have the following structures: wherein R 1 is selected from the gr…

Assignees

Inventors

Classifications

  • Chemistry & Metallurgy · mapped topic

  • Chemistry & Metallurgy · mapped topic

  • Chemistry & Metallurgy · mapped topic

  • Chemistry & Metallurgy · mapped topic

  • C07D307/46Primary

    Chemistry & Metallurgy · mapped topic

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What does patent US9758499B2 cover?
A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the sub…
Who is the assignee on this patent?
Univ Florida State Res Found
What technology area does this patent fall under?
Primary CPC classification C07D307/46. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Sep 12 2017 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 5 related publications on this page (citations in our corpus or others sharing the same primary CPC).