57213-26-0Relevant academic research and scientific papers
Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects
Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin
, (2020/12/07)
A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.
Metal-Free tert -Butyl Hydrogenperoxide (TBHP) Mediated Radical Alkylation of Enol Acetates with Alcohols: A New Route to β-Hydroxy Ketones
Tang, Yucai,Fan, Yuanyuan,Zhang, Ye,Li, Xiaoqing,Xu, Xiangsheng
, p. 1860 - 1863 (2016/07/16)
A metal-free TBHP-mediated radical alkylation of enol acetates with alcohols is described. This method provides a new route to a variety of β-hydroxy-ketones in moderate to good yields.
Synthesis of silaoxazolinium salts bearing weakly coordinating anions: Structures and catalytic activities in the aldol reaction
Chandra Sheker Reddy, Anugu,Chen, Zhang,Hatanaka, Tohru,Minami, Tatsuya,Hatanaka, Yasuo
, p. 3575 - 3582 (2013/07/26)
The synthesis and structures of silaoxazolinium salts 2 and their application to the catalytic Mukaiyama aldol reaction are described. The reaction of (N-amidomethyl)dimethylchlorosilane (1a) or (N-amidomethyl) bis(trimethylsilyl)chlorosilane (1b) with me
Unusual tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes
Maifeld, Sarah V.,Lee, Daesung
, p. 4995 - 4998 (2007/10/03)
(Chemical Equation Presented) An unusual tandem reaction sequence to form oxasilacyclopentenes from carbonyls and alkynylsilanes in the presence of a catalytic amount of nucleophilic initiator has been discovered. The reaction proceeds readily at room tem
Diastereoselective reactions at enantiomerically pure, sterically congested cyclohexanes as an entry to wailupemycins A and B: Total synthesis of (+)-wailupemycin B
Kirsch, Stefan F.,Bach, Thorsten
, p. 7007 - 7023 (2007/10/03)
Wailupemycin A (1) and B (2) are polyketide natural products with a highly substituted cyclohexanone core. Three different routes for the syntheses of these compounds were pursued, which commenced from either (R)-(-)-carvone (ent-5) or (S)-(+)-carvone (5)
Strong counteranion effects on the catalytic activity of cationic silicon lewis acids in Mukaiyama aldol and Diels-Alder reactions
Hara, Kenji,Akiyama, Ryuto,Sawamura, Masaya
, p. 5621 - 5623 (2007/10/03)
(Graph Presented) A toluene-coordinated silyl borate, [Et 3Si(toluene)]B(C6F5)4, demonstrated catalytic activities significantly higher than those of Me3SiOTf and Me3SiNTf2 in Mu
A high yield procedure for the Me3SiNTf2-induced carbon-carbon bond-forming reactions of silyl nucleophiles with carbonyl compounds: The importance of addition order and solvent effects
Ishihara,Hiraiwa,Yamamoto
, p. 1851 - 1854 (2007/10/03)
We demonstrate the efficiency of Me3SiNTf2 (0.3-1.0 mol%) as a strong Lewis acid catalyst for the Mukaiyama aldol and Sakurai-Hosomi allylation reactions, and that the slow addition of carbonyl compounds to a solution of acid catalys
Aluminum bis(trifluoromethylsulfonyl)amides: New highly efficient and remarkably versatile catalysts for C-C bond formation reactions
Marx, Andreas,Yamamoto, Hisashi
, p. 178 - 181 (2007/10/03)
Superacid-derived aluminum catalysts R2AlNTf2 (2-5 mol%) are highly efficient and versatile and are suitable promoters for the allylation and pentadienylation of aldehydes, aldol reactions, aldol cross-coupling of ketones, and Michae
Highly controlled chemoselectivity of tin enolate by its hybridization state. Anionic complex of tin enolate coordinated by tetrabutylammonium bromide as halo selective reagent
Yasuda, Makoto,Hayashi, Keiko,Katoh, Yasuhiro,Shibata, Ikuya,Baba, Akio
, p. 715 - 721 (2007/10/03)
The control of reactivity and/or selectivity of organotin(IV) enolates has been studied by means of a high coordination method in which the hybridization state of tin was effectively changed. An anionic tin complex, five-coordinated tin enolate 1(h), was formed by the coordination of bromide anion from tetrabutylammonium bromide (Bu4NBr) to neutral four-coordinated tin(IV) enolates 1(e). The highly coordinated enolates which attained a marked change in chemoselectivity have higher nucleophilicity to organic halides. In addition, they showed low nucleophilicity toward carbonyl moieties by the coordination of the bromide anion, whereas carbonyl addition readily proceeds using the usual four-coordinated tin enolate. NMR studies revealed the generation of HMPA- or bromide-anion-coordinated tin enolates in equilibrium between four-coordinated enolate 1c(e) and five-coordinated enolate 1c(h), showing a considerable upfield shift δ(119Sn) and increasing values of the coupling constants 1J(119Sn-13C). In detailed NMR analyses of highly coordinated tin enolate, it was shown that the contribution of highly coordinated species 1(h) to the equilibrium between 1(e) and 1(h) became more significant as the added amount of ligands such as Bu4NBr or HMPA was increased. Considering these results, it was assumed that the bromide-anion-coordinated tin enolate was generated, which showed a unique reactivity and selectivity. The effective control of chemoselectivity in the intermolecularly competitive reaction between organic halides and carbonyl compounds was demonstrated using two types of tin enolates, four-coordinated enolate and highly coordinated anionic enolate; halide displacement reaction exclusively took place using the bromide-anion-coordinated enolate, and the usual four-coordinated enolates reacted with only carbonyl compounds.
