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

被引：1
|
作者：
Jiang, Lin [1 ]
Yu, Liu-Dong [1 ]
Peng, Pei-Ying [1 ]
Li, Hong-Li [1 ]
Jiang, Deng-Bang [1 ]
Wang, Yi-Dan [1 ]
Yuan, Ming-Long [1 ]
Yuan, Ming-Wei [1 ]
机构：
[1] Yunnan Minzu Univ, Sch Chem & Environm, Natl & Local Joint Engn Res Ctr Green Preparat Te, Kunming 650031, Yunnan, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 03期
基金：
中国国家自然科学基金;
关键词：
Allylic nitro compound; Morita-Baylis-Hillman carbonate; 1; 3-dienylation; allylic alkylation; denitration; CHEMISTRY; 1,3-DIENES; ACCESS;
D O I：
10.1080/00397911.2020.1832526
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：419 / 427
页数：9
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