Enantioselective Conjugate Additions of "Difficult" Ketones to Nitrodienynes and Tandem Annulations. Issue 1 (14th December 2016)

• Record Type: Journal Article
• Authors: Liu, Teng; Zhou, Mingxin; Yuan, Tengrui; Fu, Binbin; Wang, Xinran; Peng, Fangzhi; Shao, Zhihui
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 1(2017)
• Page Start: 89
• Page End: 95
• Publication Date: 2016-12-14
• Subjects: acetone -- aromatic ketones -- conjugate addition -- nitrodienynes -- tandem annulations; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600849
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The first enantioselective conjugate additions of problematic aromatic ketones and acetone to nitrodienynes have been achieved by employing a chiral multifunctional primary amine catalyst recently developed by us. The reactions took place in a 1, 4‐manner. Furthermore, by utilizing the resulting chiral functionalized 1, 3‐enynes as a starting point, we have developed unprecedented p ‐toluenesulfonic acid‐catalyzed tandem annulations, which allow the efficient and selective construction of various synthetically useful cyclic 1, 5‐diketones (R=Ar) and dienones (R=Me). Abstract :