Direct Synthesis of Cycloalkanes from Diols and Secondary Alcohols or Ketones Using a Homogeneous Manganese Catalyst - INAC-SCIB Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2019

Direct Synthesis of Cycloalkanes from Diols and Secondary Alcohols or Ketones Using a Homogeneous Manganese Catalyst

Résumé

A method for the synthesis of substituted cycloalkanes was developed using diols and secondary alcohols or ketones via a cascade hydrogen borrowing sequence. A non-noble and air-stable manganese catalyst (2 mol %) was used to perform this transformation. Various substituted 1,5-pentanediols (3−4 equiv) and substituted secondary alcohols (1 equiv) were investigated to prepare a collection of substituted cyclohexanes in a diastereoselective fashion. Similarly, cyclopentane, cyclo-hexane, and cycloheptane rings were constructed from substituted 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol, and sterically hindered ketones following a (4 + 1), (5 + 1), and (6 + 1) strategy, respectively. This reaction provides an atom economic methodology to construct two C−C bonds at a single carbon center generating high-value cycloalkanes from readily available alcohols as feedstock using an earth-abundant metal catalyst.
Fichier principal
Vignette du fichier
28 - JACS Mn cycloclkanes Leitner.pdf (1.04 Mo) Télécharger le fichier
Origine : Publication financée par une institution
Loading...

Dates et versions

hal-02367932 , version 1 (09-11-2020)

Identifiants

Citer

Akash Kaithal, Lisa-Lou Gracia, Clément Camp, Elsje Alessandra Quadrelli, Walter Leitner. Direct Synthesis of Cycloalkanes from Diols and Secondary Alcohols or Ketones Using a Homogeneous Manganese Catalyst. Journal of the American Chemical Society, 2019, 141 (44), pp.17487-17492. ⟨10.1021/jacs.9b08832⟩. ⟨hal-02367932⟩
49 Consultations
265 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More