Synlett 2018; 29(19): 2456-2460
DOI: 10.1055/s-0037-1610552
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© Georg Thieme Verlag Stuttgart · New York

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

Saitanya K. Bharadwaj
a  Department of Chemistry, Pragjyotish College, Guwahati, Assam 781009, India
,
Siddheshwar K. Bankar
b  Organic 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
,
b  Organic 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
› Author Affiliations
IISER Mohali is acknowledged for funding and for providing the infrastructure. S.K.B (first author) thanks IASc-INSA-NASI FAST-SF 2018. S.K.B. (second author) thanks IISER Mohali for a fellowship.
Further Information

Publication History

Received: 15 June 2018

Accepted: 10 July 2018

Publication Date:
02 August 2018 (online)

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.

 
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