Regioselective metallation and alkylation/acylation of 2-aryl-1,3-dioxanes was achieved in high yield.
Stereoelectronic effects on metallation of 1,3-dioxanes
β Scribed by A.I. Meyers; Arthur L. Campbell; Anthony G. Abatjoglou; Ernest L. Eliel
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 205 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Metallation of the acetal (H-2) proton in 1,3-dioxolanes, 1,3-dioxanes and open chain acetals is possible only if the proton can occupy an "equatorial-like" conformation.
π SIMILAR VOLUMES
The stereoelectronically controlled reaction of P-methoxy-1,3-dioxane (1) with Grignard reagents does not follow the course suggested by the behavior of anancomeric models for the conformational isomers of 1. Treatment of 1 with RMgX leads to the predominant formation of acid labile 3-(l'-methoxyalk
The synthesis and the stereocbemistry of a new class of compounds showing atropisomerism, the 1,3-dioxane derivatives bearing disymmetric axial aryl groups in position 2 of the 1,3-dioxane ring are reported.