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2‐Pentylcyclopent‐2‐en‐1‐one by Catalytic Pauson‐Khand Reaction
Author(s) -
Rautenstrauch Valentin,
Mégard Patrick,
Conesa José,
Küster Wilhelm
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199014131
Subject(s) - cyclopentenone , catalysis , yield (engineering) , pauson–khand reaction , chemistry , alkene , ethylene , medicinal chemistry , organic chemistry , materials science , metallurgy
Only 0.0022 mole equivalents of the catalyst [Co 2 (CO) 8 ] are necessary for the preparation of the cyclopentenone 1 from 1‐heptyne, ethylene, and CO with an exchange number of about 220. This first catalytic Pauson‐Khand reaction (PKR) with an unstrained alkene affords 1 , a precursor of methyl‐ trans ‐dihydrojasmonate that is important for the perfumery industry, in about 50% yield. The main byproducts of this PKR were also identified and possible routes for their formation proposed.