Rhodium(I)-Catalyzed Enantioselective Ring-Opening and Isomerization of Cyclobutanols through a (

Molecular Structure Rhodium Ketones Stereoisomerism Isomerism Catalysis

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
14 Jul 2023
Historique:
medline: 17 7 2023
pubmed: 3 7 2023
entrez: 3 7 2023
Statut: ppublish

Résumé

A rhodium(I)-catalyzed highly enantioselective ring-opening and isomerization of cyclobutanols has been developed. The reaction provides a mild, atom-economical, and redox-neutral approach for the synthesis of chiral acyclic ketones bearing a β-tertiary stereocenter. Excellent enantioselectivities and high yields can be achieved using cyclobutanols with alkoxy substituents at the C3 position. Mechanistic studies reveal that cyclobutanol only undergoes intramolecular hydrogen migration, and the formation of a (

Identifiants

DOI: 10.1021/acs.orglett.3c01870 PMID: 37394755
pubmed: 37394755
doi: 10.1021/acs.orglett.3c01870
doi:

Substances chimiques

Rhodium DMK383DSAC
cyclobutanol 0
Ketones 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

5151-5156

Auteurs

Jianzhong Lu (J)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Mengzhen Zhang (M)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Xinxin Zheng (X)

Institute of Pharmaceutical Science, China Pharmaceutical University, Nanjing 210009, P. R. China.

Pei Shen (P)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Yuemeng Xu (Y)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Qian Zhang (Q)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Yixin Tang (Y)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.

Guozhu Zhang (G)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.
ORCID: 0000-0002-2222-6305

Rui Guo (R)

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei 430079, P. R. China.
ORCID: 0000-0002-7436-8436

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Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Rhodium(I)-Catalyzed Enantioselective...
questionsmedicales.fr › Produits chimiques inorganiques › Métaux › Métaux lourds › Rhodium › Rhodium(I)-Catalyzed Enantioselective...
questionsmedicales.fr › Composés chimiques organiques › Cétones › Rhodium(I)-Catalyzed Enantioselective...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Rhodium(I)-Catalyzed Enantioselective...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Rhodium(I)-Catalyzed Enantioselective...
questionsmedicales.fr › Phénomènes chimiques › Catalyse › Rhodium(I)-Catalyzed Enantioselective...