Facile Access to Cyclopentadienes via Catalytic Intramolecular Palladium-Ene Reaction of 2,4-Pentadienyl Acetates

Saitanya K. Bharadwaj; Siddheshwar K. Bankar; S. S. V. Ramasastry

doi:10.1055/s-0037-1610552

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(19): 2456-2460
DOI: 10.1055/s-0037-1610552

synpacts

Facile Access to Cyclopentadienes via Catalytic Intramolecular Palladium-Ene Reaction of 2,4-Pentadienyl Acetates

Saitanya K. Bharadwaj

^aDepartment of Chemistry, Pragjyotish College, Guwahati, Assam 781009, India

,

Siddheshwar K. Bankar

^bOrganic Synthesis and Catalysis Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research(IISER) Mohali, Knowledge City, Sector 81, S. A. S. Nagar, Manauli PO, Punjab 140306, India eMail: ramsastry@iisermohali.ac.in

,

S. S. V. Ramasastry *

^bOrganic Synthesis and Catalysis Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research(IISER) Mohali, Knowledge City, Sector 81, S. A. S. Nagar, Manauli PO, Punjab 140306, India eMail: ramsastry@iisermohali.ac.in

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Abstract

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Abstract

We have recently disclosed a palladium-catalyzed Trost–Oppolzer type Alder-ene reaction of 2,4-pentadienyl acetates for the synthesis of highly substituted cyclopentadienes and cyclopentene-fused aromatics. The overall transformation also represents an acid-free iso-Nazarov type cyclization. Herein, we provide the hypothesis and rationale behind this work, while highlighting the seminal contributions of Trost, Oppolzer and others towards the development of the palladium-ene reaction.

Key words

Tsuji–Trost reaction - metallo-ene reaction - iso-Nazarov reaction - natural products - annulation - cyclopentanes

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