Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (

Carbon Cycloaddition Reaction Cyclopentanes Indenes Stereoisomerism

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
01 07 2022
Historique:
pubmed: 15 6 2022
medline: 6 7 2022
entrez: 14 6 2022
Statut: ppublish

Résumé

A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with α-alkylated electron-deficient alkenes bearing Oppolzer's camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this reaction was demonstrated in the concise formal synthesis of (

Identifiants

DOI: 10.1021/acs.joc.2c00753 PMID: 35699729
pubmed: 35699729
doi: 10.1021/acs.joc.2c00753
doi:

Substances chimiques

Cyclopentanes 0
Indenes 0
puraquinonic acid 0
Carbon 7440-44-0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

8788-8795

Auteurs

Miho Oga (M)

Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Yusei Takamatsu (Y)

Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Akihiro Ogura (A)

Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
ORCID: 0000-0002-4793-5706

Ken-Ichi Takao (KI)

Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
ORCID: 0000-0001-8629-1002

Articles similaires

Environmental impact assessment of Flora and its role in offsetting carbon along National Highway-16, India.

H Ramamohan, S Raminaidu, I Sudhakara Rao et al.
1.00
India Carbon Sequestration Environmental Monitoring Carbon Biomass

Use of dislodgeable foliar residue studies for the evaluation of isomerization potential of active substances for non-dietary risk assessment.

Silke Wagner, Christian J Kuster
1.00
Risk Assessment Plant Leaves Isomerism Humans Stereoisomerism

Potential of biochar to restoration of microbial biomass and enzymatic activity in a highly degraded semiarid soil.

Francisco L A Barbosa, João M R Santos, Jaedson C A Mota et al.
1.00
Charcoal Soil Microbiology Soil Biomass Carbon

Transcriptome Analysis of Chinese Cabbage Infected with Plasmodiophora Brassicae in the Primary Stage.

Huihui Wang, Jing Zhang, Yilian Wang et al.
1.00
Plasmodiophorida Plant Diseases Gene Expression Regulation, Plant Gene Expression Profiling Brassica

Classifications MeSH

questionsmedicales.fr › Produits chimiques inorganiques › Éléments › Carbone › Asymmetric Synthesis of Cyclopentene Compounds...
questionsmedicales.fr › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Réaction de cycloaddition › Asymmetric Synthesis of Cyclopentene Compounds...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures cycliques › Hydrocarbures alicycliques › Cyclopentanes › Asymmetric Synthesis of Cyclopentene Compounds...
questionsmedicales.fr › Composés polycycliques › Hydrocarbures aromatiques polycycliques › Indènes › Asymmetric Synthesis of Cyclopentene Compounds...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Asymmetric Synthesis of Cyclopentene Compounds...