Stereoselective allylic 1, 3-dienylation of Morita–Baylis–Hillman carbonates via an alkylation–denitration sequence. Issue 3 (1st February 2021)

• Record Type: Journal Article
• Authors: Jiang, Lin; Yu, Liu-Dong; Peng, Pei-Ying; Li, Hong-Li; Jiang, Deng-Bang; Wang, Yi-Dan; Yuan, Ming-Long; Yuan, Ming-Wei
• Is Part Of: Synthetic communications. Volume 51:Issue 3(2021)
• Page Start: 419
• Page End: 427
• Publication Date: 2021-02-01
• Subjects: Allylic nitro compound -- Morita–Baylis–Hillman carbonate -- 1, 3-dienylation -- allylic alkylation -- denitration; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1832526
• Languages: English
• ISSNs: 0039-7911

Abstract

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: