A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles
نویسندگان
چکیده
3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple efficient method to access analogs of these compounds that are armed with rich functionality allowing them be chemoselectively derivatized high diastereocontrol.
منابع مشابه
Stereoselectively fluorinated N-heterocycles: a brief survey
The stereoselective incorporation of fluorine atoms into N-heterocycles can lead to dramatic changes in the molecules' physical and chemical properties. These changes can be rationally exploited for the benefit of diverse fields such as medicinal chemistry and organocatalysis. This brief review will examine some of the effects that fluorine substitution can have in N-heterocycles, including cha...
متن کاملEnantioselective Pd-catalyzed hydrogenation of fluorinated imines: facile access to chiral fluorinated amines.
An enantioselective hydrogenation of simple fluorinated imines has been developed using Pd(OCOCF(3))(2)/(R)-Cl-MeO-BIPHEP as a catalyst, and up to 94% ee was achieved. This method provides an efficient route to enantioenriched fluorinated amines.
متن کاملAdditive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles
An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic in...
متن کاملPractical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions
The Pd(TFA)2-catalyzed [4+1] annulation of chained or cyclic α-alkenyl-dicarbonyl compounds and unprotected primary amines for “one-pot” synthesis of pyrroles is reported here. Enamination and amino-alkene were involved in this practical and efficient tandem reaction. The annulation products were isolated in moderate to excellent yields with O2 as the terminal oxidant under mild conditions. In ...
متن کاملSynthesis of Saturated Five-Membered Nitrogen Heterocycles via Pd-Catalyzed C N Bond-Forming Reactions
Saturated five-membered nitrogen heterocycles, such as pyrrolidines, indolines, and isoxazolidines, appear as subunits in a broad array of biologically active and medicinally significant molecules [1]. As such, the synthesis of these compounds has been of longstanding interest. Many classical approaches to the construction of these heterocycles involve the use of C N bond-forming reactions such...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c00752