4 research outputs found
Rhodium/Chiral Diene Complexes in the Catalytic Asymmetric Arylation of β‑Pyrazol-1-yl Acrylates
The asymmetric conjugate
addition of arylboronic acids to substituted
and unsubstituted β-pyrazol-1-yl (<i>E</i>)-<i>tert</i>-butyl acrylates <b>4</b> catalyzed by 5 mol %
of the RhÂ(I)/diene <b>2a</b> catalyst provided the corresponding
addition products in 44–98% yield and 91–>99.5% ee.
The method was applied to the formal synthesis of (3<i>S</i>)-3-aryl-3-(pyrazol-1-yl)Âpropanoic acid <b>1b</b> with agonistic
activity toward the human GPR40 G-protein coupled receptor
Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β‑Nitroolefins: Formal Synthesis of (<i>S</i>)‑SKF 38393
An efficient enantioselective addition of an array of arylboronic
acids to various β-nitrostyrenes catalyzed by a novel and reactive
rhodium–diene catalyst (S/C up to 1000) was developed, providing
β,β-diarylnitroethanes in good to high yields (62–99%)
with excellent enantioselectivities (85–97% ee). The method
was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly
providing the desired products with high enantioselectivities and
yields. The usefulness of this method was demonstrated in the formal
synthesis of the enantiomer of the dopamine receptor agonist and antagonist,
SKF 38393
Enantioselective and Rapid Rh-Catalyzed Arylation of <i>N</i>‑Tosyl- and <i>N</i>‑Nosylaldimines in Methanol
Enantiomerically
enriched tosyl-protected diarylmethylamines were
rapidly prepared by the asymmetric addition of arylboronic acids to <i>N</i>-tosylaldimines under mild conditions in the presence of
a catalyst prepared in situ from RhÂ(I) and a chiral diene ligand.
This methodology offers access to diarylmethylamines in good yields
with excellent chiral purity at room temperature using MeOH as a solvent
and NEt<sub>3</sub> as a base. Its synthetic utility was demonstrated
by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(<b>14</b>), an antagonist of the <i>N</i>-methyl-d-aspartate (NMDA) receptor
Enantioselective and Rapid Rh-Catalyzed Arylation of <i>N</i>‑Tosyl- and <i>N</i>‑Nosylaldimines in Methanol
Enantiomerically
enriched tosyl-protected diarylmethylamines were
rapidly prepared by the asymmetric addition of arylboronic acids to <i>N</i>-tosylaldimines under mild conditions in the presence of
a catalyst prepared in situ from RhÂ(I) and a chiral diene ligand.
This methodology offers access to diarylmethylamines in good yields
with excellent chiral purity at room temperature using MeOH as a solvent
and NEt<sub>3</sub> as a base. Its synthetic utility was demonstrated
by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(<b>14</b>), an antagonist of the <i>N</i>-methyl-d-aspartate (NMDA) receptor