Platinum‐Catalyzed Isomerization of Cyclopropenes to 1,3‐Dienes

Author:

Smyrnov Vladyslav1ORCID,Homassel Antonin1,Choudhury Leander1,Waser Jerome1ORCID

Affiliation:

1. Laboratory of Catalysis and Organic Synthesis Institute of Chemical Sciences and Engineering École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LCSO, BCH 4306 1015 Lausanne Switzerland

Abstract

AbstractHerein we report a platinum‐catalyzed isomerization of cyclopropenes to 1,3‐dienes. Diverse dienylated alcohols were obtained in 42–98 % yield. The synthetic potential of the products was demonstrated by their use in Diels–Alder cycloadditions with various dienophiles. Isotope labelling studies provide strong support for a mechanism involving pericyclic [1,5]‐σ‐bond rearrangement of a vinyl platinum carbene intermediate.

Funder

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Publisher

Wiley

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