111171-92-7Relevant academic research and scientific papers
Rhodium-Catalyzed Remote C(sp3)?H Borylation of Silyl Enol Ethers
Li, Jie,Qu, Shuanglin,Zhao, Wanxiang
supporting information, p. 2360 - 2364 (2020/01/02)
A rhodium-catalyzed remote C(sp3)?H borylation of silyl enol ethers (SEEs, E/Z mixtures) by alkene isomerization and hydroboration is reported. The reaction exhibits mild reaction conditions and excellent functional-group tolerance. This method is compatible with an array of SEEs, including linear and branched SEEs derived from aldehydes and ketones, and provides direct access to a broad range of structurally diverse 1,n-borylethers in excellent regioselectivities and good yields. These compounds are precursors to various valuable chemicals, such as 1,n-diols and aminoalcohols.
A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling
Weigel, William K.,Dennis, Taylor N.,Kang, Amrik S.,Perry, J. Jefferson P.,Martin, David B. C.
, p. 6234 - 6238 (2018/10/05)
A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.
Enantioselective α-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway
Conrad, Jay C.,Kong, Jongrock,Laforteza, Brian N.,MacMillan, David W. C.
supporting information; experimental part, p. 11640 - 11641 (2009/12/08)
(Chemical Equation Presented) The intramolecular-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent electron-rich aromatics and heterocycles thus efficiently providing cyclic α-aryl aldehyde products (10 examples: ≥70% yield and ≥90% ee). In accordance with our radical mechanism, when there is a choice between arylation at the ortho or para position of anisole substrates, we find that arylation proceeds selectively at the ortho position.
Friedel-Crafts Cyclialkylations of Some Epoxides. 3. Cyclizations of Tertiary and Meta-Substituted Arylalkyl Epoxides
Taylor, Stephen K.,Blankespoor, Curtis L.,Harvey, Suzanne M.,Richardson, Lynell J.
, p. 3309 - 3312 (2007/10/02)
The intramolecular cyclization of aryl groups to tertiary epoxide position was investigated, and the results were used to test the applicability of Baldwin's rules to this specific class of reactions.As a probe into mechanism of reactions studied earlier, the cyclizations of some meta-substituted 1,2-epoxy-5-phenylpentanes were examined to determine positional selectivities.The data obtained were compared with those of other studies, and comments are made on the reaction mechanism.
AROMATIC ANNULATION WITH BISPHENYLTHIONIUM IONS
Manas, Abdul Rahman Bin,Smith, Robin A. J.
, p. 1847 - 1856 (2007/10/02)
The chemospecific production and intramolecular aromatic electrophilic substitution (annulation) of bis(phenylthio)carbocations (bisphenylthionium ions) has been studied using appropriate model compounds.The annulation reaction is very sensitive to the Lewis acid initiator and also the solvent.The best reaction conditions were found to be a suspension of silver trifluoromethanesulfonate in dichloromethane.Annulation of six-membered rings onto alkylbenzene and five- and seven-membered rings onto activated benzenes have been achieved.
