Base‐Catalyzed Stereoselective 1, 6‐Conjugated Addition/Aromatization of P(O)–H Compounds with para‐Quinone Methides. Issue 20 (24th May 2019)

• Record Type: Journal Article
• Authors: Xiong, Biquan; Wang, Gang; Zhou, Congshan; Liu, Yu; Xu, Weifeng; Xu, Wen‐Yuan; Yang, Chang‐An; Tang, Ke‐Wen
• Is Part Of: European journal of organic chemistry. Issue 20(2019)
• Page Start: 3273
• Page End: 3282
• Publication Date: 2019-05-24
• Subjects: Quinones -- Phosphorylation -- Synthetic methods -- Nucleophilic addition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900419
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A versatile base‐catalyzed method for the 1, 6‐conjugated addition/aromatization of para ‐quinone methides with P(O)–H compounds is illustrated. Further studies on this reaction by using optically active H ‐phosphinates show that the reaction takes place stereospecifically with retention or inversion of configuration at the phosphorus center. It is a simple way to produce a broad spectrum of functionalized phosphane oxides and phosphinates from basic P(O)–H starting materials. This finding also contributes significantly to the stereosynthesis in the catalysis. Abstract : A versatile base‐catalyzed 1, 6‐conjugated addition/aromatization of P(O)–H compounds with p ‐QMs is described. This protocol avoids the use of metal catalysis and air‐sensitive reagents and has a broad substrate scope. The optically active H ‐phosphinates could react with p ‐QMs stereospecifically with retention (R 3 = Ph, mesityl) or inversion (R 3 = Bn) of the configuration at the phosphorus center.