72469-77-3Relevant academic research and scientific papers
The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
Chen, Weiqiang,Fang, Huaquan,Xie, Kaixue,Oestreich, Martin
supporting information, p. 15126 - 15129 (2020/10/23)
An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Haya
Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin
supporting information, p. 1135 - 1140 (2019/01/11)
The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.
Metal-Free Transfer Hydrobromination of C-C Triple Bonds
Chen, Weiqiang,Oestreich, Martin
supporting information, p. 4531 - 4534 (2019/06/27)
A transfer hydrobromination of C-C triple bonds inititated by Br?nsted acids is reported. Hydrogen bromide is released stepwise from a bench-stable cyclohexa-1,4-diene-based surrogate, generating biphenyl and ethylene as waste. A range of vinyl bromides was prepared from terminal and internal, mainly acceptor-substituted alkynes with good functional-group tolerance.
Multicomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydes
Bykova, Tetiana,Al-Maharik, Nawaf,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information, p. 1117 - 1123 (2016/01/15)
This paper reports the preparation of methyl substituted all-cis tetrafluorocyclohexanes prepared from a Birch reduction of benzoic acid, worked up with a methyl iodide quench. The resultant methylcyclohexadiene carboxylic acid was reduced to the alcohol,
Diastereoselective hydroformylation of 2,5-cyclohexadienyl-1-carbinols with catalytic amounts of a reversibly bound directing group
Usui, Ippei,Nomura, Kenichi,Breit, Bernhard
supporting information; experimental part, p. 612 - 615 (2011/04/26)
A phosphinite plays a role as a reversibly bound directing group for the regio-and diastereoselective hydroformylation of 2,5-cyclohexadienyl-1- carbinols. Of the two alkene functions only one was functionalized through hydroformylation to form a syntheti
A chemoenzymatic approach to the taxoid BC-substructure
Arseniyadis, Simeon,Yashunsky, Dmitry V.,Munoz Dorado, Manuel,Brondi Alves, Rosemeire,Wang, Qian,Potier, Pierre,Toupet, Loic
, p. 6215 - 6232 (2007/10/03)
The synthesis of a homochiral taxoid BC-unit containing the required functionalities on the B-ring periphery and a conveniently functionalized C-ring moiety by combination of enzymatic hydrolysis and the aldol-annelation-fragmentation sequence is describe
Studies towards the total synthesis of taxoids. A straightforward procedure for the taxoid BC substructure
Arseniyadis,Yashunsky,Munoz Dorado,Brondi Alves,Toromanoff,Toupet,Potier
, p. 4927 - 4930 (2007/10/02)
The aldol condensation of the ketone 6 and the aldehyde 7 followed by an annelation-fragmentation afforded the bicyclo[6.4.0][dodecane derivative 3 with the appropriate functionalities for further elaboration.
