1560-02-7Relevant articles and documents
Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization
Zhao, Shibin,Gensch, Tobias,Murray, Benjamin,Niemeyer, Zachary L.,Sigman, Matthew S.,Biscoe, Mark R.
, p. 670 - 674 (2018/11/01)
Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed.
Stereochemistry of the thermal isomerizations of (1/R,2R)-1-((E)-Styryl)-2-methylcyclopropane to 3-phenyl-4-methylcyclopentenes
Baldwin, John E.,Bonacorsi Jr., Samuel
, p. 10621 - 10627 (2007/10/02)
(1A,2R)-1-((E)-Styryl)-2-methylcyclopropane at 250 °C racemizes and isomerizes to 6-phenylhexa-1,4-(Z)-diene and to the four isomers of 3-phenyl-4-methylcyclopentene. From the measured rate constants for racemization and for structural isomerizations, and
Organoyttrium-catalyzed cyclization of substituted 1,5- and 1,6-dienes
Molander, Gary A.,Hoberg, John O.
, p. 3123 - 3125 (2007/10/02)
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