3 research outputs found
Catalytic Asymmetric Synthesis of Tro虉ger鈥檚 Base Analogues with Nitrogen Stereocenter
Nitrogen stereocenters are common chiral units in natural
products,
pharmaceuticals, and chiral catalysts. However, their research has
lagged largely behind, compared with carbon stereocenters and other
heteroatom stereocenters. Herein, we report an efficient method for
the catalytic asymmetric synthesis of Tro虉ger鈥檚 base
analogues with nitrogen stereocenters via palladium catalysis and
home-developed GF-Phos. It allows rapid construction
of a new rigid cleft-like structure with both a C- and a N-stereogenic
center in high efficiency and selectivity. A variety of applications
as a chiral organocatalyst and metallic catalyst precursors were demonstrated.
Furthermore, DFT calculations suggest that the NH路路路O
hydrogen bonding and weak interaction between the substrate and ligand
are crucial for the excellent enantioselectivity control
Catalytic Asymmetric Synthesis of Tro虉ger鈥檚 Base Analogues with Nitrogen Stereocenter
Nitrogen stereocenters are common chiral units in natural
products,
pharmaceuticals, and chiral catalysts. However, their research has
lagged largely behind, compared with carbon stereocenters and other
heteroatom stereocenters. Herein, we report an efficient method for
the catalytic asymmetric synthesis of Tro虉ger鈥檚 base
analogues with nitrogen stereocenters via palladium catalysis and
home-developed GF-Phos. It allows rapid construction
of a new rigid cleft-like structure with both a C- and a N-stereogenic
center in high efficiency and selectivity. A variety of applications
as a chiral organocatalyst and metallic catalyst precursors were demonstrated.
Furthermore, DFT calculations suggest that the NH路路路O
hydrogen bonding and weak interaction between the substrate and ligand
are crucial for the excellent enantioselectivity control
Diastereo- and Enantioselective Construction of Dihydrobenzo[<i>e</i>]indole Scaffolds via Catalytic Asymmetric [3 + 2] Cycloannulations
The first catalytic
asymmetric construction of chiral dihydrobenzo颅[<i>e</i>]颅indole
scaffolds has been established in a highly diastereo-
and enantioselective mode (30 examples, up to 99% yield, >95:5
dr,
>99% ee), which makes use of chiral phosphoric acid-catalyzed [3
+
2] cycloannulations of azonaphthalene derivatives with 3-vinylindoles.
This reaction also represents the first catalytic asymmetric cycloannulation
of azonaphthalene derivatives with alkenes, which will not only provide
a useful method for constructing enantioenriched dihydrobenzo颅[<i>e</i>]颅indole scaffolds but also advance the chemistry of catalytic
asymmetric reactions of azonaphthalene derivatives