Stereo controlled synthesis of (E,Z)-dienals via tandem Rh(I) catalyzed propargyl claisen rearrangement
US9758499B2 · kind B2 · utility
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Key dates
| Filing date | Jan 4, 2017 |
| Grant date | Sep 12, 2017 |
| Priority date | — |
| Expiry date | Jan 4, 2037 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D307/42
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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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