6932-61-2Relevant academic research and scientific papers
Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
Chen, Jingjia,Hu, Weipeng,Jin, Jing,Lovinger, Gabriel J.,Morken, James P.,Zhang, Chenlong
supporting information, p. 14189 - 14195 (2021/09/11)
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
Cis-specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway
Emer, Enrico,Pfeifer, Lukas,Brown, John M.,Gouverneur, Veronique
supporting information, p. 4181 - 4185 (2014/05/06)
This paper describes the hydrofluorination of alkenes through sequential H- and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed. See attached PdF: A series of benzylic fluorides was prepared by hydrofluorination which proceeds through a PdII/IV catalytic manifold. The method is mechanistically distinct from previously reported radical hydrofluorination, and is characterized by its clean regioselectivity and unique cis stereospecificity. The first example of enantioselective net HF addition onto 2-vinylnaphthalene is also disclosed.
Stereochemical proof for front side deuteride attack via σ-sulfurane in the reductive desulfinylation of sulfoxides with lithium aluminum deuteride
Sagae, Takahiro,Ogawa, Satoshi,Furukawa, Naomichi
, p. 4043 - 4046 (2007/10/02)
Stereochemical results obtained from the concomitant reduction and desulfinylation of 1-phenyl-2-pyridyl-2(p-tolysulfinyl)- and 1,2-diphenyl-2-phenylsulfinyl ethanols with lithium aluminum deuteride reveal that the reactions proceed stereospecifically via
STUDIES OF PYRAZINES. PART 8. PYROLYSIS OF 2-ALKOXYPYRAZINES; SUBSTITUENT EFFECTS AND STEREOSPECIFICITY
Konakahara, Takeo,Sato, Kenji,Takagi, Yukio,Kuwata, Kazuhiko
, p. 641 - 646 (2007/10/02)
Twelve 2-alkoxypyrazines (R=iPr, sBu, 1,2-dimethylpropyl, 1,2,2-trimethylpropyl, t-butyl, t-pentyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, octyl, neopentyl, +/--erythro- and +/--threo-2-deuterio-1,2-diphenylethyl) have been pyrolysed to elucidate the substituent effects on the rate and stereospecificity of the reaction.Activation parameters (log A and Ea) for the first eight compounds listed were determined.The reaction was accelerated by α-substitution; this was a combination of both polar and steric effects.The stereospecificity of the reaction was high.
