2 research outputs found
Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α‑Aminophosphonates
The widespread occurrence and synthetic
accessibility
of amides
render them valuable precursors for the synthesis of diverse nitrogen-containing
compounds. Herein, we present a metal-free and streamlined synthetic
strategy for the synthesis of quaternary α-aminophosphonates.
This approach involves sequential deoxygenative nucleophilic phosphonation
and versatile electrophilic alkylation of secondary amides in a one-pot
fashion. Notably, this method enables the direct bis-functionalization
of secondary amides with both nucleophiles and electrophiles for the
first time, with simple derivatization leading to valuable free α-aminophosphonates
by hydrolysis. The protocol has the advantages of operational simplicity,
broad functional-group compatibility, environmental friendliness,
and scalability to multigram quantities
Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of α‑Substituted β‑Ketoesters via Dynamic Kinetic Resolution
An
iridium/f-amphol catalytic system for the enantioselective hydrogenation
of α-substituted β-ketoesters via dynamic kinetic resolution
is reported. The desired <i>anti</i> products were obtained
in high yields (up to 98%) with good diastereoselectivity (up to 96:4
diastereometic ratio (dr)) and excellent enantioselectivity (up to
>99% enantiomeric excess (ee)). A catalytic model is proposed to
explain
the stereoselectivity