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Base‐Catalyzed Stereoselective 1,6‐Conjugated Addition/Aromatization of P(O)–H Compounds with para ‐Quinone Methides
Author(s) -
Xiong Biquan,
Wang Gang,
Zhou Congshan,
Liu Yu,
Xu Weifeng,
Xu WenYuan,
Yang ChangAn,
Tang KeWen
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900419
Subject(s) - aromatization , chemistry , catalysis , conjugated system , quinone , stereoselectivity , base (topology) , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , polymer , mathematical analysis , mathematics
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.