764583-30-4Relevant academic research and scientific papers
Enantiospecific, regioselective cross-coupling reactions of secondary allylic boronic esters
Chausset-Boissarie, Laetitia,Ghozati, Kazem,Labine, Emily,Chen, Jack L.-Y.,Aggarwal, Varinder K.,Crudden, Cathleen M.
supporting information, p. 17698 - 17701 (2014/01/17)
An original syn: The first enantioselective Suzuki-Miyaura cross-coupling of chiral, enantioenriched secondary allylic boronic esters is described (see scheme; DME=dimethoxyethane, Bpin = pinacolboryl, dba = dibenzylideneacetone). Mechanistic studies show that the reactions proceed via γ-selective transmetalation followed by reductive elimination. The reaction provides the first independent confirmation that the transmetalation of boronic esters proceeds via a syn pathway. Copyright
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.
Enantioselective synthesis of chiral sulfones by Rh-catalyzed asymmetric addition of boronic acids to α,β-unsaturated 2-pyridyl sulfones
Mauleon, Pablo,Alonso, Ines,Rivero, Marta Rodriguez,Carretero, Juan C.
, p. 9924 - 9935 (2008/03/28)
(Chemical Equation Presented) A general and efficient method for the rhodium-catalyzed enantioselective catalytic conjugate addition of organoboronic acids to α,β-unsaturated sulfones is described. The success of the process relies on the use of α,β-unsat
