A one‐pot synthesis of tetrasubstituted acrylaldehydes
Palladium‐catalyzed allylic alkylation of 2‐aryl‐1,3‐dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with
- NSF-PAR ID:
- 10080458
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Advanced Synthesis & Catalysis
- Volume:
- 361
- Issue:
- 3
- ISSN:
- 1615-4150
- Page Range / eLocation ID:
- p. 502-509
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
Abstract via difunctionalization of aryl propynyl ethers has been achieved, which involves a trifluoromethylthiolation process and a radical 1,4‐aryl migration from oxygen to carbon. The reaction shows excellent conversion of aryl propynyl ethers into trifluoromethyl‐containing α,β‐unsaturated aldehydes through a radical pathway.magnified image -
Abstract We evaluated the influence of solvent on the alumina‐promoted C3‐alkylation of indoles with α,β‐unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3‐alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty‐four examples with reaction yields ranging from 61 to 96%.
magnified image -
Abstract A simple one‐pot synthesis of
β ‐hydroxyallenamides is reported. This procedure entails chemo‐ and regioselective hydroboration of 3‐en‐1‐ynyl‐sulfonylamides with Cy2BH followed by homoallenylation of aldehydes to yield β‐hydroxyallenamides (up to 94% yield and >20:1 dr). Controlled synthesis of up to three continuous stereochemical elements was realized. Density functional theory (DFT) calculations suggest a concerted Zimmerman‐Traxler chair‐like transition state. Initial results suggest that enantio‐ and diastereoselective synthesis of β‐hydroxyallenamides with optically active hydroboration reagents is viable.magnified image -
Abstract The enantioselective palladium‐catalyzed decarboxylative allylic alkylation of fully substituted α‐hydroxy acyclic enol carbonates providing tetrasubstituted benzoin derivatives is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochemically rich derivatives.
magnified image -
Abstract Pseudocyclic β‐trifluorosulfonyloxy vinylbenziodoxolones were prepared starting from hydroxybenziodoxolones and alkynes in the presence of trifluoromethanesulfonic acid. The reaction of these compounds with azide anion leads to β‐azido vinylbenziodoxolones as products of vinylic nucleophilic substitution in which addition‐elimination reactions occur and the double bond configuration is retained. The structures of β‐trifluorosulfonyloxy vinylbenziodoxolone and β‐azido vinylbenziodoxolone were established by single crystal X‐ray diffraction.
magnified image