The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Feb. 21, 2017

Filed:

May. 28, 2015
Applicants:

The Florida State University Research Foundation, Inc., Tallahassee, FL (US);

Robert A. Holton, Tallahassee, FL (US);

Inventors:

Dinesh V. Vidhani, Tallahassee, FL (US);

Marie E. Krafft, Tallahassee, FL (US);

Igor Alabugin, Tallahassee, FL (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07C 41/08 (2006.01); C07C 45/51 (2006.01); C07C 253/30 (2006.01); C07D 307/42 (2006.01); C07D 307/46 (2006.01);
U.S. Cl.
CPC ...
C07C 45/513 (2013.01); C07C 41/08 (2013.01); C07C 253/30 (2013.01); C07D 307/42 (2013.01); C07D 307/46 (2013.01);
Abstract

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.


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