Unknown

Dataset Information

0

Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams.


ABSTRACT: The enantioselective synthesis of nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines, including the total synthesis of natural products and medicinal chemistry. In this Article, we describe the highly enantioselective palladium-catalysed decarboxylative allylic alkylation of readily available lactams to form 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related lactams. Given the prevalence of quaternary N-heterocycles in biologically active alkaloids and pharmaceutical agents, we envisage that our method will provide a synthetic entry into the de novo asymmetric synthesis of such structures. As an entry for these investigations we demonstrate how the described catalysis affords enantiopure quaternary lactams that intercept synthetic intermediates previously used in the synthesis of the Aspidosperma alkaloids quebrachamine and rhazinilam, but that were previously only available by chiral auxiliary approaches or as racemic mixtures.

SUBMITTER: Behenna DC 

PROVIDER: S-EPMC3266627 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

altmetric image

Publications

Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams.

Behenna Douglas C DC   Liu Yiyang Y   Yurino Taiga T   Kim Jimin J   White David E DE   Virgil Scott C SC   Stoltz Brian M BM  

Nature chemistry 20111218 2


The enantioselective synthesis of nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines, including the total synthesis of natural products and medicinal chemistry. In this Article, we describe the highly enantioselective palladium-catalysed decarboxylative allylic alkylation of readily available lactams to form 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related lactams. Giv  ...[more]

Similar Datasets

| S-EPMC5555155 | biostudies-literature
| S-EPMC4640231 | biostudies-literature
| S-EPMC6103296 | biostudies-literature
| S-EPMC6410707 | biostudies-literature
| S-EPMC7942817 | biostudies-literature
| S-EPMC5632216 | biostudies-literature
| S-EPMC8162308 | biostudies-literature
| S-EPMC7608871 | biostudies-literature
| S-EPMC4078409 | biostudies-literature
| S-EPMC2804400 | biostudies-literature