Stereo controlled synthesis of (E,Z)-dienals via tandem Rh(I) catalyzed propargyl claisen rearrangement
AssigneeThe Florida State University Research Foundation, Inc.
InventorsDinesh V. Vidhani, Marie E. Krafft, Igor Alabugin
Life of this patent
Estimating the term…
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.
Claims8
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
- R1 is selected from the group consisting of C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-12 cycloalkyl, C3-12 cycloalkenyl, C6-24 aryl, C3-18 heteroaryl, amino, and C1-12 alkylamino;
- and
- R2 is selected from the group consisting of C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-12 cycloalkyl, C3-12 cycloalkenyl, C6-24 aryl, C3-18 heteroaryl, amino, and C1-12 alkylamino.
Dependencies are inferred from the claim text.