414869-14-0Relevant articles and documents
A catalytic and enantioselective desymmetrization of meso cyclic allylic bisdiethylphosphates with organozinc reagents
Piarulli, Umberto,Daubos, Philippe,Claverie, Christelle,Roux, Maryline,Gennari, Cesare
, p. 234 - 236 (2003)
The chosen one: The desymmetrization of meso-2 is possible with the use of diethylzinc in the presence of the Cu' complex of 1 (10 mol%; Tf = CF3SO2). Ligand 1 was optimized from a screen of a library of 125 compounds. Other ligands
Ligand-controlled selectivity in the desymmetrization of meso cyclopenten-1,4-diols via rhodium(I)-Catalyzed addition of arylboronic acids
Menard, Frederic,Perez, David,Sustac Roman, Daniela,Chapman, Timothy M.,Lautens, Mark
supporting information; experimental part, p. 4056 - 4068 (2010/08/07)
A highly enantioselective desymmetrization of meso cyclopent-2-ene-1,4- diethyl dicarbonates has been developed using a Rh-catalyzed asymmetric allylic substitution. Depending on the type of ligand used, each of two regioisomeric products can be obtained in good yield and excellent enantioselectivity. Under rhodium(I) catalysis, bisphosphine P-Phos ligands form trans-1,2- arylcyclopentenols as the major product, whereas Segphos ligands lead predominantly to trans-1,4-arylcyclopentenols.
Palladium-catalyzed γ-selective and stereospecific allyl-aryl coupling between acyclic allylic esters and arylboronic acids
Ohmiya, Hirohisa,Makida, Yusuke,Li, Dong,Tanabe, Masahito,Sawamura, Masaya
supporting information; experimental part, p. 879 - 889 (2010/03/25)
Reactions between acyclic (E)-allylic acetates and arylboronic acids in the presence of a palladium catalyst prepared from Pd(OAc)2, phenanthroline (or bipyridine), and AgSbF6 (1:1.2:1) proceeded with excellent γ-selectivity to afford allyl-aryl coupling products with E-configuration. The reactions of α-chiral allylic acetates took place with excellent α-to-γ chirality transfer with syn stereochemistry to give allylated arenes with a stereogenic center at the benzylic position. The reaction tolerated a broad range of functional groups in both the allylic acetates and the arylboronic acids. Furthermore, γ-arylation of cinnamyl alcohol derivatives afforded gem-diarylalkane derivatives containing an unconjugated alkenic substituent. The synthetic utility of this method was demonstrated by its utilization in an efficient synthesis of (+)-sertraline, an antidepressant agent. The observed γ-regioselectivity and E-1,3-syn stereochemistry were rationalized based on a Pd(II) mechanism involving transmetalation between a cationic mono(acyloxo)palladium(II) complex and arylboronic acid, and directed carbopalladation followed by syn-β-acyloxy elimination. The results of stoichiometric reactions of palladium complexes related to possible intermediates were fully consistent with the proposed mechanism.
Rhodium-catalysed substitutive arylation of cis-allylic diols with arylboroxines
Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
, p. 595 - 597 (2007/10/03)
Substitutive arylation of cis-allylic diols occurs upon treatment with arylboroxines in the presence of a rhodium(i) catalyst; the reaction proceeds through the addition of an intermediate arylrhodium(i) species across the carbon-carbon double bond and su
