13891-95-7Relevant articles and documents
Iridium-catalyzed carbonyl allylation by allyl ethers with tin(II) chloride
Masuyama, Yoshiro,Marukawa, Masanori
, p. 5963 - 5965 (2007)
3-Alkoxypropenes, namely allyl ethers such as allyl butyl ether, allyl 2-hydroxypropyl ether, and diallyl ether, serve as reagents for the allylation of aldehydes with tin(II) chloride in the presence of a catalytic amount of [IrCl(cod)]2 in TH
Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions
Andrews, Philip C.,Peatt, Anna C.,Raston, Colin L.
, p. 243 - 248 (2004)
Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were al
Additive effects of ligand activated allylation of aldehydes by allyltrichlorosilane
Short, Joanne D.,Attenoux, Sandrine,Berrisford, David J.
, p. 2351 - 2354 (1997)
The rate of allylation of aldehydes using a combination of allyltrichlorosilane and O-donor ligands can he profoundly accelerated by the addition of a range of simple tetra-n-butylammonium salts. Measured tin values decrease from over 6 hours under define
Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
Apolinar, Omar,Derosa, Joseph,Engle, Keary M.,Karunananda, Malkanthi K.,Kleinmans, Roman,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
supporting information, p. 5311 - 5316 (2021/07/26)
A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Benaglia, Maurizio,Benincori, Tiziana,Raimondi, Laura Maria,Rossi, Sergio
, p. 535 - 546 (2020/03/27)
This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.
Axially chiral N,N′-dioxides ethers for catalysis in enantioselective allylation of aldehydes
Wu, Shijie,Xing, Yongfei,Wang, Jie,Guo, Xingchen,Zhu, Huajie,Li, Wan
supporting information, p. 947 - 957 (2019/08/30)
A series of axially chiral ethers synthesized from biscarboline N,N′-dioxides, (S)-1a to (S)-1n, was investigated in enantioselectivity addition reactions of allyltrichlorosilane with a series of substituted aldehydes, including bulky substituted aldehydes. High enantioselectivities (up to 96%ee) were achieved using the catalyst (S)-1k at 1 mol % loading.
