Expanded Helicenes as Synthons for Chiral Macrocyclic Nanocarbons.

Macrocyclic Compounds / chemical synthesis Polycyclic Compounds / chemistry Stereoisomerism

Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
24 06 2020
Historique:
pubmed: 27 5 2020
medline: 14 5 2021
entrez: 27 5 2020
Statut: ppublish

Résumé

Expanded helicenes are large, structurally flexible π-frameworks that can be viewed as building blocks for more complex chiral nanocarbons. Here we report a gram-scale synthesis of an alkyne-functionalized expanded [11]helicene and its single-step transformation into two structurally and functionally distinct types of macrocyclic derivatives: (1) a figure-eight dimer via alkyne metathesis (also gram scale) and (2) two arylene-bridged expanded helicenes via Zr-mediated, formal [2+2+

Identifiants

DOI: 10.1021/jacs.0c03177 PMID: 32450694
pubmed: 32450694
doi: 10.1021/jacs.0c03177
doi:

Substances chimiques

Macrocyclic Compounds 0
Polycyclic Compounds 0
helicenes 0

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

11084-11091

Subventions

Organisme : NIH HHS
ID : S10 OD024998
Pays : United States
Organisme : NIH HHS
ID : S10 OD025102
Pays : United States

Auteurs

Gavin R Kiel (GR)

Department of Chemistry, University of California, Berkeley, California 94720, United States.
ORCID: 0000-0001-6449-8547

Katherine L Bay (KL)

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
ORCID: 0000-0002-9917-8188

Adrian E Samkian (AE)

Department of Chemistry, University of California, Berkeley, California 94720, United States.

Nathaniel J Schuster (NJ)

Department of Chemistry, Columbia University, New York, New York 10027, United States.

Janice B Lin (JB)

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
ORCID: 0000-0002-9333-5760

Rex C Handford (RC)

Department of Chemistry, University of California, Berkeley, California 94720, United States.
ORCID: 0000-0002-3693-1697

Colin Nuckolls (C)

Department of Chemistry, Columbia University, New York, New York 10027, United States.
ORCID: 0000-0002-0384-5493

K N Houk (KN)

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
ORCID: 0000-0002-8387-5261

T Don Tilley (TD)

Department of Chemistry, University of California, Berkeley, California 94720, United States.
ORCID: 0000-0002-6671-9099

Articles similaires

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

Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers.

Xuan Liao, Cancan Lu, Yaning Duan et al.
1.00
Glutamine Stereoisomerism Spectrometry, Fluorescence Colorimetry Carbon

Cross-chiral exponential amplification of an RNA enzyme.

Wesley G Cochrane, Grant A L Bare, Gerald F Joyce et al.
1.00
RNA, Catalytic Stereoisomerism RNA Ligase (ATP) Nucleic Acid Conformation RNA

Enhancing antibacterial efficacy through macrocyclic host complexation of fluoroquinolone antibiotics for overcoming resistance.

Suchitra D Panigrahi, Karoline C Klebba, Emily N Rodriguez et al.
1.00
Anti-Bacterial Agents Fluoroquinolones Macrocyclic Compounds Drug Resistance, Bacterial Microbial Sensitivity Tests

Classifications MeSH

Recherchemedicale.com › Composés polycycliques › Composés macrocycliques › Expanded Helicenes as Synthons for Chiral...
Recherchemedicale.com › Composés polycycliques › Expanded Helicenes as Synthons for Chiral...
Recherchemedicale.com › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Expanded Helicenes as Synthons for Chiral...