67221-16-3Relevant academic research and scientific papers
An efficient and facile access to substituted 1e,3e-dienylphosphonates via horner-wadsworth-emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate
Yahyaoui, Marwa,Touil, Soufiane,Samarat, Ali
supporting information, p. 729 - 731 (2018/05/22)
An operationally simple and high-yielding synthetic method for 1E,3E-dienylphosphonates has been developed through the Horner-Wadsworth-Emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate, in heterogeneous medium, in th
Copper(I)-Catalyzed Enantioselective 1,6-Borylation of α,β,γ,δ-Unsaturated Phosphonates
Lee, Hyesu,Yun, Jaesook
supporting information, p. 7961 - 7964 (2019/01/14)
Copper(I)-catalyzed asymmetric 1,6-borylation of 1,3-dienylphosphonates was achieved using (S,S)-Ph-BPE as a chiral ligand. Regio-, stereo-, and enantioselective borylation successfully proceeded to afford phosphonate-containing allylboronates, with high enantioselectivity up to 97% ee. Further applications of the resulting products generated a valuable phosphonate analogue of γ-butyrolactone.
Stereoselective synthesis of dienyl phosphonates via extended tethered ring-closing metathesis
Schmidt, Bernd,Kunz, Oliver
supporting information, p. 4470 - 4473 (2013/09/24)
Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.
New and efficient synthesis of 1,3-dienylphosphonates by palladium-catalyzed substitution of propargylic esters to diethyl phosphite
Liu, Xiao-Ning,Guo, Wei-Lei,Hou, Chuan-Jin,Hu, Xiang-Ping
, p. 2622 - 2626 (2013/07/26)
An efficient route to the synthesis of 1,3-dienylphosphonates (1) has been developed for the first time by the substitution of propargylic esters (2) to the diethyl phosphite (3) nucleophile in the presence of Pd2 (dba) 3 · CHCl3 (2 mol %) and 2,2′- bis(diphenylphosphino)-1,1′-binaphthyl (4 mol%). Both the alkyl and aryl 1,3-dienylphosphonates can be prepared from this transformation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Reaction of diethyl thiocyanatomethylphosphonate with aldehydes as a route to diethyl Z-1-alkenylphosphonates
Blaszczyk, Roman,Gajda, Tadeusz
, p. 732 - 739 (2008/03/18)
Diastereoselective synthesis of diethyl Z-1-alkenylphosphonates from easily available diethyl thiocyanatomethylphosphonate and aromatic aldehydes has been developed. Olefination of the aldehydes occurs under mild conditions and affords the title compounds with moderate yields. A plausible mechanism of the above-mentioned reaction is also discussed.
Conjugate addition of lithiated Schollkopf's bislactim ether to 1E,3E-Butadienylphosphonates: Stereocontrolled access to 2,3 -anti-4E 2-Amino-6-phosphono-4-hexenoic acid derivatives
Ojea, Vicente,Conde, Susana,Ruiz, Maria,Fernandez, Ma Carmen,Quintela, Jose Ma
, p. 4311 - 4314 (2007/10/03)
Face-selective 1,6-addition of lithiated Schollkopf's bislactime ether 5 to 4-substituted, 1,4- or 3,4-disubstituted 1E,3E-butadienylphosphonates 6a-d allows a direct and stereocontrolled access to semi-rigid AP6 analogues, the 2,3-anti-4E 2-amino-6-phosphono-4-hexenoic acid derivatives 4a-c. The relative stereochemistry was assigned from a NMR study of the cyclic derivative 12c. Tenmembered trans-fused chair-boat-like transition states are invoked to rationalize the stereochemical outcome of the addition.
Preparation of new wittig reagents and their application to the synthesis of α,β-unsaturated phosphonates
Xu, Yibo,Flavin, Michael T.,Xu, Ze-Qi
, p. 7697 - 7701 (2007/10/03)
The Wittig reagent [(diethoxyphosphinyl)methylidene]triphenylphosphorane (1b) has been successfully synthesized for the first time via its phosphonium triflate salt (4a), by treating (diethoxyphosphinyl)methyl triflate with triphenylphosphine. The procedure has been applied to the synthesis of other phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various aldehydes and an activated ketone, affording the corresponding α,β-unsaturated phosphonates. Triphenylphosphorane 1b and triphenylphosphonium 4a led to both cis and trans isomers with the latter being predominant, while trans isomers were almost exclusively formed when tributyl reagents (1c and 4d) were used.
