Journal
SYNTHETIC COMMUNICATIONS
Volume 51, Issue 3, Pages 419-427Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2020.1832526
Keywords
Allylic nitro compound; Morita-Baylis-Hillman carbonate; 1; 3-dienylation; allylic alkylation; denitration
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Funding
- National Natural Science Foundation of China [21302163]
- Project of Innovative Research Team of Yunnan Province [2017HC034]
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A two-step metal-free process has been developed for the stereoselective allylic 1,3-dienylation of Morita-Baylis-Hillman (MBH) carbonates under mild reaction conditions. This transformation involves allylic alkylation with MBH carbonates followed by denitration, resulting in allylic 1,3-dienyl MBH derivatives with exclusive (E)-selectivity.
A two-step, metal-free process for stereoselective allylic 1,3-dienylation of Morita-Baylis-Hillman (MBH) carbonates under mild reaction conditions has been developed. Using cyclic allylic nitro compounds as potential dienylating reagents, the transformation proceeds through tertiary amine-catalyzed allylic alkylation with MBH carbonates (14 examples, up to 94% yield), followed by AcOH-mediated denitration (12 examples, up to 87% yield), affording allylic 1,3-dienyl MBH derivatives with exclusive (E)-selectivity.
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