130888-99-2Relevant academic research and scientific papers
First DMAP-mediated direct conversion of Morita-Baylis-Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates
Ayadi, Marwa,Elleuch, Haitham,Vrancken, Emmanuel,Rezgui, Farhat
supporting information, p. 2906 - 2915 (2017/01/09)
An efficient synthesis of a series of γ-ketoallylphosphonates through a direct conversion of both primary and secondary Morita-Baylis-Hillman (MBH) alcohols by trialkyl phosphites with or without DMAP, used as additive, and under solvent-free conditions, is described herein for the first time. Subsequently, a highly regioselective Luche reduction of the primary phosphonate 2a (R = H) gave the corresponding γ-hydroxyallylphosphonate 5 that further reacted with tosylamines in the presence of diiodine (15 mol %) as a catalyst, affording the corresponding SN2-type products 6a-d in 63 to 70% isolated yields. Alternatively, the alcohol 5 produced the corresponding acetate 7 which, mediated by Ce(III), was successfully converted into the corresponding γ-aminoallylphosphonates 8a-d.
Simple and advantageneous stereoselective synthesis of (Z)-allyl phosphonates starting from Baylis-Hillman adducts
Das, Biswanath,Bhunia, Nisith,Damodar, Kongara
experimental part, p. 2479 - 2489 (2012/07/28)
(Chemical Equation Presented) Baylis-Hillman adducts 3-hydroxyl-2-methylene alkanoates have been converted in one pot into the corresponding (Z)-allyl phosphonates by treatment with FeCl3 and trialkyl phosphites in toluene under reflux. The pro
Nucleophilic addition of triethyl phosphite to acetates of the Baylis-Hillman adducts: Stereoselective synthesis of (E)- and (Z)-allylphosphonates
Basavaiah, Deevi,Pandiaraju, Subramanian
, p. 2261 - 2268 (2007/10/03)
Nucleophilic addition of triethyl phosphite to 3-acetoxy-2-methylenealkanenitriles and methyl 3-acetoxy-2-methylenealkanoates provides (2E)-2-(diethoxyphosphorylmethyl)alk-2-enenitriles and methyl (2Z)-2-(diethoxyphosphorylmethyl)alk-2-enoates respectively with good stereoselectivity.
A Convenient Method for the Synthesis of Substituted 2-Methoxycarbonyl- and 2-Cyanoallylphosphonates. The Allyl Phosphite - Allylphosphonate Rearrangement
Janecki, Tomasz,Bodalski, Ryszard
, p. 799 - 801 (2007/10/02)
The thermally induced Arbuzov rearrangement of allyl diethyl phosphites gives, under unprecedented mild conditions, a variety of diethyl allylphosphonates with high stereoselectivity and in high yield.
