We have developed a Pt(COD)Cl(2)-catalyzed hydrative cyclization of 1,6-diynes leading to the formation of functionalized cyclohexenones in good yields.
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http://dx.doi.org/10.3390/molecules15075045 | DOI Listing |
J Org Chem
January 2023
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, Uttar Pradesh, India.
Cascade or domino reactions serve as a powerful technique for the synthesis of complex organic scaffolds in one pot. Herein, a Cu(II)-catalyzed and silica gel-assisted multicomponent reaction (MCR) between bromoalkyne-tethered cyclohexadienones, amides, and water for the construction of hexahydrobenzofuran-3-carboxamide is developed. The reaction proceeds via a C-N coupling reaction followed by hydrative cyclization of ynamide intermediates.
View Article and Find Full Text PDFOrg Lett
December 2019
Institut de Chimie des Substances Naturelles , CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 av. de la Terrasse , 91198 Gif-sur-Yvette , France.
This study discloses the first enantioselective variant of the gold(I)-catalyzed hydrative cyclizations of ynamides, which have been implemented by using bis-gold(I) complexes of chiral diphosphines. Starting from -propargyl-ynamides and water in the presence of -toluenesulfonic acid, the cyclization reactions afford -tosyl-3,6-dihydropyridin-2(1)-ones in good isolated yields and with high levels of stereocontrol (20 examples, enantiomeric ratios up to 94:6).
View Article and Find Full Text PDFChemistry
July 2013
School of Chemistry, University of Hyderabad, Hyderabad-500046, India.
Org Lett
August 2011
Department of Chemistry and the Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
A new hydrative cyclization of 1,7- and 1,8-diynyl ethers is reported. Using catalytic InI(3) and p-TSA as a cocatalyst, several 2,2-disubstituted tetrahydrofurans with exocyclic enone appendages were prepared. Reaction optimization and scope, mechanistic insight, and further transformation to a C-nucleoside analog are presented.
View Article and Find Full Text PDFChem Commun (Camb)
February 2011
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.
A ruthenium cyclic biscarbene complex reacted with a H(2)O molecule under mild conditions to produce η(5)-oxapentadienyl complex, that proved to be the intermediate in the catalytic hydrative cyclization of a diyne.
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