One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o -quinone methide with unactivated dienes

Tetrahedron ◽  
2016 ◽  
Vol 72 (47) ◽  
pp. 7642-7649 ◽  
Author(s):  
Jian Liu ◽  
Xiaoxiao Wang ◽  
Lubin Xu ◽  
Zhihui Hao ◽  
Liang Wang ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Quinone Methide ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
One Step ◽  
Electron Demand

Total synthesis of (–)-xyloketal D and its enantiomer — Confirmation of absolute stereochemistry

2004 ◽  
Vol 82 (11) ◽  
pp. 1640-1648 ◽  
Author(s):  
Jeremy D Pettigrew ◽  
Rebecca P Freeman ◽  
Peter D Wilson
Keyword(s):  
Total Synthesis ◽  
Mannich Base ◽  
Alder Reaction ◽  
Diels Alder ◽  
Quinone Methide ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
The Absolute ◽  
Electron Demand ◽  
Absolute Stereochemistry

The total synthesis of (–)-xyloketal D and its enantiomer have been achieved by the reaction of an ortho-quinone methide with (4R)- and (4S)-4,5-dihydro-2,4-dimethylfuran via a diastereoselective inverse electron demand Diels–Alder reaction. This total synthesis confirmed the absolute stereochemistry of the natural product. The ortho-quinone methide was generated by reaction of an appropriately functionalized Mannich base with methyl iodide. The Mannich base was prepared in one step from 2,4-dihydroxyacetophenone, formaldehyde, and morpholine. The enantiomeric dihydrofurans were prepared from (2R)- and (2S)-2-methylpent-4-ynoic acid via a three-step reaction sequence. These chiral nonracemic synthetic precursors were prepared from the corresponding (R)-phenylglycinol-derived diastereomeric amides of the readily available racemic carboxylic acid. The absolute stereochemistry of these carboxylic acids was firmly established by conversion to a known compound that had been previously prepared from a chiral pool starting material.Key words: xyloketal D, inverse electron demand Diels–Alder reaction, ortho-quinone methide, dihydrofuran.

Single wall carbon nanotube (SWCNT)–gold nanorod (AuNR) conjugates via thermally-mild reaction conditions

2017 ◽  
Vol 41 (21) ◽  
pp. 12392-12396 ◽  
Author(s):  
Siting Ni ◽  
Jun Zhu ◽  
Mohamed Amine Mezour ◽  
R. Bruce Lennox
Keyword(s):  
Carbon Nanotube ◽  
Covalent Binding ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gold Nanorod ◽  
Reaction Conditions ◽  
Single Wall Carbon ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

A thermally-mild method for covalent binding of SWCNTs to AuNRs, based on an inverse-electron-demand Diels–Alder reaction, is established and discussed.

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