Highly enantioselective one-pot sequential synthesis of valerolactones and pyrazolones bearing all-carbon quaternary stereocentres. Issue 7 (2nd February 2021)

• Record Type: Journal Article
• Authors: Xu, Yan-Li; Qin, Zhou-Zhou; Wang, Yu-Xia; Zhao, Peng-Fei; Li, Hong-Feng; Du, Zhi-Hong; Da, Chao-Shan
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 7(2021)
• Page Start: 1610
• Page End: 1615
• Publication Date: 2021-02-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob02489a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Highly enantiopure and bioactive δ-valerolactones and pyrazolones, bearing α-all-carbon quaternary stereocentres, were successfully and sequentially prepared via a one-pot procedure catalysed by a new chiral squaramide under mild reaction conditions. Abstract : Highly enantiopure and bioactive δ-valerolactones and pyrazolones, bearing α-all-carbon quaternary stereocentres, were successfully and sequentially prepared via a one-pot procedure starting from readily available, inexpensive materials, catalysed by a new chiral squaramide under mild reaction conditions. An organocatalytic Michael reaction afforded the valerolactones, while a one-pot Michael-hydrazinolysis-imidization cascade yielded the pyrazolones. This procedure is economically efficient and environmentally benign.