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Updated: Apr 28, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Sequential Diels-Alder reaction/rearrangement sequence: synthesis of functionalized bicyclo[2.2.1]heptane derivatives
Demin Liang1, Yue Zou, Quanrui Wang
1Department of Chemistry, Fudan University , 220 Handan Road, Shanghai 200433, People's Republic of China.
Abstract:
A sequential Diels-Alder reaction/rearrangement sequence was developed for the synthesis of diverse functionalized bicyclo[2.2.1]heptanes as novel floral and woody odorants. The outcome of the rearrangement depended on the substitution pattern of the dienes. 2D NMR analysis has established the correct relative configuration of the bicyclo[2.2.1]heptanone, which was originally misassigned. Furthermore, when the initiating DA reaction was catalyzed by a chiral Lewis acid, the bicyclo[2.2.1]heptane derivatives including (+)-herbanone can be obtained in an enantiomeric ratio (er) up to 96.5:3.5.
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