93433-54-6Relevant academic research and scientific papers
Selective C-alkylation Between Alcohols Catalyzed by N-Heterocyclic Carbene Molybdenum
Liu, Jiahao,Li, Weikang,Li, Yinwu,Liu, Yan,Ke, Zhuofeng
supporting information, p. 3124 - 3128 (2021/09/20)
The first implementation of a molybdenum complex with an easily accessible bis-N-heterocyclic carbene ligand to catalyze β-alkylation of secondary alcohols via borrowing-hydrogen (BH) strategy using alcohols as alkylating agents is reported. Remarkably high activity, excellent selectivity, and broad substrate scope compatibility with advantages of catalyst usage low to 0.5 mol%, a catalytic amount of NaOH as the base, and H2O as the by-product are demonstrated in this green and step-economical protocol. Mechanistic studies indicate a plausible outer-sphere mechanism in which the alcohol dehydrogenation is the rate-determining step.
Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata
Pinedo-Rivilla, Cristina,Aleu, Josefina,Collado, Isidro G.
experimental part, p. 1653 - 1657 (2012/01/30)
The transformation of (E)-2-benzylideneindan-1-one 1 by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata as biocatalysts was studied. The results showed the catalytic potential of these fungi in affording several hydroxylation a
Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea
Pinedo-Rivilla, Cristina,Aleu, Josefina,Grande Benito, Manuel,Collado, Isidro G.
experimental part, p. 3784 - 3789 (2010/09/06)
Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1R,2S)-2-Benzylindan-1-ol ((1R,2S)-2) and (S)-2-benzylindan-1-one ((S)-3) were produced by fermenting baker's yeast. Li
Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
Ishimaru, Takehisa,Shibata, Norio,Horikawa, Takao,Yasuda, Naomi,Nakamura, Shuichi,Toru, Takeshi,Shiro, Motoo
supporting information; experimental part, p. 4157 - 4161 (2009/03/11)
(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.
Studies on the chemistry of 2-(2-oxo-3-phenylpropyl)-benzaldehydes: Novel total synthesis of 3-phenylnaphthalen-2-ols and 2-hydroxy-3-phenyl-1,4- naphthoquinones
Martínez, Ana,Fernández, Marcos,Estévez, Juan C.,Estévez, Ramón J.,Castedo, Luis
, p. 485 - 492 (2007/10/03)
We describe the first studies on the chemistry of 2-(2-oxo-3-phenylpropyl) benzaldehydes, which were converted into 3-benzylisochromen-1-ones via the corresponding 2-(2-oxo-3-phenylpropyl)benzoic acid. The 2-(2-oxo-3-phenylpropyl) benzaldehydes proved to be convenient starting materials for the synthesis of 3-phenyl-2-naphthols. Oxidation of the latter compounds resulted in a novel, efficient synthesis of 3-phenyl-1,2-naphthoquinones, which were efficiently transformed into 2-hydroxy-3-phenyl-1,4-naphthoquinones.
On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2s,3s)-3-bromo-4-phenylbutan-2- ol
Aleu, Josephina,Fronza, Giovanni,Fuganti, Claudio,Perozzo, Valentina,Serra, Stefano
, p. 1589 - 1596 (2007/10/03)
Fermenting baker's yeast converts α-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4- phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)- allylic alcohol 17 prevalently.
Hydroxy-Directed Hydroaluminations: A Stereoselective Approach to Cycloalkanols From β-Aryl Enones.
Koch, Kevin,Smitrovich, Jacqueline H.
, p. 1137 - 1140 (2007/10/02)
Various aryl substituted enones are reduced using lithium aluminum hydride to afford sterioselectively trans substituted alkanols.Mechanistic studies demonstrate 1,2-addition followed by hydroxy-directed hydroalumination of the conjugated styryl unit.
Undirectional Triple and Double Hydrogen Rearrangement Reactions in the Radical Cations of γ-Arylalkanols
Kuck, Dietmar,Filges, Ulrich
, p. 643 - 653 (2007/10/02)
A novel fragmentation reaction accompanied by the unidirectional migration of three hydrogen atom has been found in the radical cations of γ-arylpropanols with electron-donating substituents in the para position.This triple hydrogen (3H) rearrangement rea
Stereospecificity of Introduction of Hydride Ion during Double Bond Reduction of 2-Benzylidene-1-tetralone and Other Related Compounds
Chatterjee, Amareshwar,Dutta, Lakshmi N.,Chatterjee, Swapan K.
, p. 955 - 960 (2007/10/02)
Lithium aluminium hydride reduction of the benzylidene derivatives (1a-c) and (5) in refluxing THF is shown to be stereospecific, the saturated alcohol isolated in each case having the trans-stereochemistry.The benzyl ketones (30a, b, d) and (7) on sodium
