1688-17-1Relevant academic research and scientific papers
Iron-Catalyzed Asymmetric Decarboxylative Azidation
Wang, Kaikai,Li, Yajun,Li, Xiaoyan,Li, Daliang,Bao, Hongli
supporting information, p. 8847 - 8851 (2021/11/24)
The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation, and reductive amination, which demonstrate the synthetic values of this reaction.
Iron catalyzed halogenation of benzylic aldehydes and ketones
Savela, Risto,W?rn?, Johan,Murzin, Dmitry Yu.,Leino, Reko
, p. 2406 - 2417 (2015/04/14)
A simple and efficient iron-catalyzed method for chlorination of aromatic carbonyl compounds is reported. By using 4-10 mol% Fe(iii) oxo acetate catalyst, prepared by solid state atmospheric oxidation of Fe(ii) acetate, in combination with triethylsilane and chlorotrimethylsilane, hydrosilylation of benzylic carbonyl compounds with subsequent chlorination is achieved within a few hours at room temperature. This new method is mild and rapid compared to the conventional two step approach involving reduction and chlorination reactions in separate stages. Development of synthetic methodology is also supplemented here by kinetic investigation of the reaction mechanism, which supports the tentative mechanisms suggested previously for similar reactions. This journal is
Dramatic Reversal of Diastereoselectivity in an N-Acyliminium Ion Cyclization Leading to Hexahydropyrroloisoquinolines. A Case of Competing Steric Interactions
Maryanoff, Bruce E.,McComsey, David F.,Almond, Harold R.,Mutter, Martin S.,Bemis, Guy W.,et al.
, p. 1341 - 1346 (2007/10/02)
The N-acyliminium ion cyclization 1 -> 2 + 3 (eq 1) with various aliphatic substituents (R = ethyl, cyclohexyl, and tert-butyl) was carried out, as an extension of our work in ref 2.The following 2:3 ratios were obtained: 39:61, 12:88, and 15:85, respecti
Syntheses of α-Phenylneopentyl Chloride Enantiomers: (S)-(-)-1-Chloro-1-phenyl-2,2-dimethylpropane from (R)-(+)-1-Phenyl-2,2-dimethyl-1-propanol via the Reaction of Tri-n-butylphosphine in Carbon Tetrachloride and (R)-(+)-1-Chloro-1-phenyl-2,2-dimethylpro
Zieger, Herman E.,Bright, Danielle Angrand,Haubenstock, H.
, p. 1180 - 1184 (2007/10/02)
(R)-(+)-1-Phenyl-2,2-dimethyl-1-propanol ((R)-(+)-α-phenylneopentyl alcohol, 1) was converted into (S)-(-)-1-chloro-1-phenyl-2,2-dimethylpropane ((S)-(-)-α-phenylneopentyl chloride, 2) by means of the tri-n-butylphosphine-carbon tetrachloride reaction.The
Alkylmetal Asymmetric Reduction. 14. Enantioselective Reduction of Ketones by Chiral (2-Methylbutyl)aluminum Derivatives
Giacomelli, Giampaolo,Lardicci, Luciano,Palla, Fabio,Caporusso, Anna Maria
, p. 1725 - 1728 (2007/10/02)
The reaction of trisaluminum with some α-alkynyl ketones has been studied: the organoaluminum derivative rapidly reduces the ketones to afford optically active α-alkynyl carbinols, which can be recovered after hydrolytic workup.The sterochemical results obtained are discussed on the basis of previous reports on enantioselective reductions of ketones by an alkylaluminum dichloride derived from β-pinene.In this context, an investigation on the reaction between a series of ketones and β-branched alkylaluminum chlorides is also reported.
Barriers to Internal Rotation in Neopentylbenzenes Substituted on the Benzyl Group. A 13C NMR Band Shape Study
Andersson, Sven,Drakenberg, Torbjoern
, p. 730 - 744 (2007/10/02)
Two series of neopentylbenzenes with one or two substituents on the benzyl group have been synthesized.In one series the substituents were H, F, Cl, Br, I, OCH3, OCOCH3, OSi(CH3)3, CH3 and CH2CH3, and in the other OH and R R = H, CH3, CH2CH3, (CH2)3CH3,
MECHANISM OF C-H INSERTION OF CARBENE IN RIGID MATRIX
Tomioka, Hideo,Ozaki, Yasuji,Izawa, Yasuji
, p. 843 - 846 (2007/10/02)
C-H insertion process of phenylchlorocarbene, a ground state singlet carbene, is not affected by matrix which generally exerts its effect in C-H insertion of most arylcarbenes.This reveals the origin of the matrix effects on carbene reactions.
