Abstract
Aims: Phosphine-catalyzed asymmetric allylic alkylation of isoxazol-5(4H)-ones with achiral Morita-Baylis-Hillman (MBH) carbonates has been developed. A series of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were obtained in 55-96% yield with 75-90% ee. Gram-scale reaction and further transformation of allylation products were conducted to demonstrate the synthetic practicability.
Methods: Under Ar atmosphere, the mixture of isoxazol-5-one 1 (0.1 mmol), MBH carbonate 2 (0.12 mmol, 1.2 equiv), catalyst P5 (10 mol%) and 4Å MS (10 mg) in toluene (1 mL) was stirred at 0 oC for 24 h. The solvent was removed under vacuum and the residue was purified by flash chromatography (petroleum ether/ethyl acetate = 3/1) to provide product 3.
Result and Conclusion: In conclusion, we have developed an efficient and enantioselective allylic alkylation of isoxazol-5(4H)-ones with achiral MBH carbonates in the presence of chiral phosphine catalyst. A broad range of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were prepared with high efficiency and enantioselectivity. Importantly, the organocatalytic δ-stereocontrol of MBH carbonates has been achieved via the synthetic strategy.
Current Organocatalysis
Title:Phosphine-Catalyzed Asymmetric Allylic Alkylation of Isoxazol-5(4H)-ones with Morita-Baylis-Hillman Carbonates
Volume: 11
Author(s): Yuncong Lei, Xuling Chen, Yantong Jiang and Pengfei Li*
Affiliation:
- Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology Guangming Advanced Research Institute, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China
Abstract:
Aims: Phosphine-catalyzed asymmetric allylic alkylation of isoxazol-5(4H)-ones with achiral Morita-Baylis-Hillman (MBH) carbonates has been developed. A series of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were obtained in 55-96% yield with 75-90% ee. Gram-scale reaction and further transformation of allylation products were conducted to demonstrate the synthetic practicability.
Methods: Under Ar atmosphere, the mixture of isoxazol-5-one 1 (0.1 mmol), MBH carbonate 2 (0.12 mmol, 1.2 equiv), catalyst P5 (10 mol%) and 4Å MS (10 mg) in toluene (1 mL) was stirred at 0 oC for 24 h. The solvent was removed under vacuum and the residue was purified by flash chromatography (petroleum ether/ethyl acetate = 3/1) to provide product 3.
Result and Conclusion: In conclusion, we have developed an efficient and enantioselective allylic alkylation of isoxazol-5(4H)-ones with achiral MBH carbonates in the presence of chiral phosphine catalyst. A broad range of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were prepared with high efficiency and enantioselectivity. Importantly, the organocatalytic δ-stereocontrol of MBH carbonates has been achieved via the synthetic strategy.
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Cite this article as:
Lei Yuncong, Chen Xuling, Jiang Yantong and Li Pengfei*, Phosphine-Catalyzed Asymmetric Allylic Alkylation of Isoxazol-5(4H)-ones with Morita-Baylis-Hillman Carbonates, Current Organocatalysis 2024; 11 () . https://dx.doi.org/10.2174/0122133372312095240607111040
DOI https://dx.doi.org/10.2174/0122133372312095240607111040 |
Print ISSN 2213-3372 |
Publisher Name Bentham Science Publisher |
Online ISSN 2213-3380 |
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