Stereoselective allylic 1,3-dienylation of Morita-Baylis-Hillman carbonates via an alkylation-denitration sequence

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...

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Bibliographic Details
Published in:Synthetic communications 2021-02, Vol.51 (3), p.419-427
Main Authors: Jiang, Lin, Yu, Liu-Dong, Peng, Pei-Ying, Li, Hong-Li, Jiang, Deng-Bang, Wang, Yi-Dan, Yuan, Ming-Long, Yuan, Ming-Wei
Format: Article
Language:English
Subjects:
1,3-dienylation
Alkylation
allylic alkylation
Allylic nitro compound
Carbonates
Denitration
Morita-Baylis-Hillman carbonate
Nitro compounds
Reagents
Selectivity
Stereoselectivity
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1832526