Lewis acid-catalyzed diels-alder reactions of peri-hydroxylated naphthoquinones: A regiochemical divergence
✍ Scribed by T.Ross Kelly; Michel Montury
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 264 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The ability of Lewis acids to enhance regioselectivity in Die16 Alder reactions between unsymmetrical dienes and dienophiles is well documented. 192 In practice, selection of the specific Lewis acid employed in any particular reaction is usually based on the unscientific but eminently pragmatic approach of trial and error. It is generally assumed, however, that
📜 SIMILAR VOLUMES
The effect of Lewis acid catalysts on the mechanism of Diels-Alder reactions is studied using the MINDO/3 method. It is found that they tend to increase the two-step character of the process through a more important participation of the charge-transfer configuration.
Diels-Alder reaction of 1,3,3-trimethyl-2-vinylcyclohexene I with conjugated ketones 2 -7 in the presence of Lewis acid leads to regto-and stereo-selective formation of bicyclic adducts 8 -13 versatile intermediates to labdanes, abietane and spongian diterpenoids.