18276-76-1Relevant academic research and scientific papers
A Stereoselective Reductive Hosomi-Sakurai Reaction
Bauer, Adriano,Maulide, Nuno
supporting information, p. 1461 - 1464 (2018/03/09)
A novel reductive variant of the classical Hosomi-Sakurai reaction is reported. This transformation hinges on a redox-neutral, stereoselective internal reduction event under mild conditions. This operationally simple reaction relies on readily available starting materials and leads to useful products in diastereoselectivities of up to 7:1. The versatility of this new method is demonstrated through the stereoselective one-step synthesis of an AChE inhibitor.
Catalyst-Free Difunctionalization of Activated Alkenes in Water: Efficient Synthesis of β-Keto Sulfides and Sulfones
Wang, Huamin,Wang, Guangyu,Lu, Qingquan,Chiang, Chien-Wei,Peng, Pan,Zhou, Jiufu,Lei, Aiwen
supporting information, p. 14489 - 14493 (2016/10/03)
Difunctionalization of activated alkenes, a powerful strategy in chemical synthesis, has been accomplished for direct synthesis of a series of β-keto sulfides and β-keto sulfones. The transformation, mediated by O2, proceeds smoothly in water and without any catalyst. Prominent advantages of this method include mild reaction conditions, purification simplicity, and gram-scale synthesis, underlining the practical utility of this methodology.
Selective Alkenylation and Hydroalkenylation of Enol Phosphates through Direct C-H Functionalization
Hu, Xu-Hong,Yang, Xiao-Fei,Loh, Teck-Peng
supporting information, p. 15535 - 15539 (2016/01/26)
An efficient and selective Rh-catalyzed direct C-H functionalization reaction of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and leads to the formation of various valuable alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The versatility and utility of the coupling products were demonstrated through further transformations into synthetically useful building blocks. P points the way: A direct C-H functionalization of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and it leads to the formation of alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The utility of the coupling products are demonstrated by further transformations into synthetically useful building blocks.
Synthesis and Herbicidal Activity of Phenylproparginols
Parlow, John J.,Clark, Robert D.
, p. 2600 - 2609 (2007/10/02)
A three-step/one-pot procedure was developed for preparing herbicidal fluorophenylproparginols from acetophenones by way of an enol phosphate intermediate.Side-by-side testing of 16 of the more active analogs showed that trans-2-methyl-1-2-(4-methoxy-2,3
Mechanism of the Reaction of Trialkyl Phosphites with α-Halogenoacetophenones in Alcoholic Solvents
Petnehazy, Imre,Keglevich, Gyoergy,Toeke, Laszlo,Hudson, Harry R.
, p. 127 - 132 (2007/10/02)
Second-order rate constants and activation parameters have been determined for the reactions of trialkyl phosphites in alcoholic media with α-chloro- or α-bromo-acetophenones having various substituents in the benzene ring (3,4-Me2, 4-Me, H, 4-Cl, and 4-I).Linear Hammett plots are consistent with the involvement of a common first intermediate in the rate-determining stage, leading to the formation of vinyl phosphate, α-hydroxyphosphonate, and acetophenone.The results provide the first kinetic evidence in support of the initial formation of the previously suggested betaine as a common intermediate in alcoholic solution.Further reaction then involves rearrangement to give the vinyloxyphosphonium species (and hence the Perkow product) or protonation followed by dealkylation to give the α-hydroxyphosphonate.Evidence for the possible formation of dehalogenated ketone via solvolysis of the α-hydroxyphosphonium intermediate is also presented.
Novel Synthetic Aspects of the Phosphonate-Phosphate-Rearrangement. II. Synthesis of Enolphosphates from 1-Oxoalkanphosphonates and Sulfur-Ylides
Hammerschmidt, Friedrich,Zbiral, Erich
, p. 1015 - 1024 (2007/10/02)
Acylphosphonates 1 react with Sulfur-ylides 2 to give enolphosphates 3 and phosphonophosphates 4.The product ratio of 3 and 4 is determined by the substituent R3.If R3 is not electronwithdrawing the phosphonophosphate 4 is the sole reaction product. - Keywords: Acylphosphonates, behaviour towards S-ylides; Rearrangement of α-hydroxyphosphonates
