Platinum-Catalyzed Cascade Rearrangement Reaction of 1,5-Diynyl Esters: Unusual Regioselective 1,5-Hydride Migration

Hui Zhu; Jiapian Huang; Congbin Fan; Zhiyuan Chen

doi:10.1002/asia.201500236

Platinum-Catalyzed Cascade Rearrangement Reaction of 1,5-Diynyl Esters: Unusual Regioselective 1,5-Hydride Migration

Chem Asian J. 2015 Jul;10(7):1463-6. doi: 10.1002/asia.201500236. Epub 2015 May 27.

Authors

Hui Zhu¹, Jiapian Huang¹, Congbin Fan², Zhiyuan Chen³

Affiliations

¹ Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China.
² Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, 330013, P. R. China).
³ Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China. [email protected].

PMID: 25929800
DOI: 10.1002/asia.201500236

Abstract

A highly regioselective sequential 1,3-acyloxy migration/pentannulation/1,5-hydride migration reaction is disclosed which provides an efficient access to (E)-2-vinyl-3-oxo-1-methyleneindenes under neutral and mild reaction conditions. The migrated hydrogen atom was derived from an unactivated alkyl group, and the long-range 1,5-H shift was confirmed through related deuterium experiments.

Keywords: 1,5-diynyl esters; 1,5-hydride migration; platinum catalysis; rearrangements; regioselective.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemical synthesis
Alkynes / chemistry
Catalysis
Cyclization
Esters / chemical synthesis
Esters / chemistry
Hydrogen / chemistry*
Indans / chemical synthesis
Indans / chemistry
Models, Molecular
Platinum / chemistry*
Stereoisomerism
Vinyl Compounds / chemical synthesis*
Vinyl Compounds / chemistry

Substances

Alkynes
Esters
Indans
Vinyl Compounds
Platinum
Hydrogen