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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 3
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Articles

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

Lin JiangNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-0453-8401View further author information
ORCID Icon,
Liu-Dong YuNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
,
Pei-Ying PengNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
,
Hong-Li LiNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
,
Deng-Bang JiangNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
,
Yi-Dan WangNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
,
Ming-Long YuanNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaView further author information
&
Ming-Wei YuanNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-6657-5048View further author information
ORCID Icon show all
Pages 419-427 | Received 03 Aug 2020, Published online: 14 Oct 2020
 
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Abstract

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.

Graphical Abstract

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The authors thank the National Natural Science Foundation of China (21302163) and Project of Innovative Research Team of Yunnan Province (2017HC034) for the financial support.

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