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Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

ABSTRACT: The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.

SUBMITTER: Halvorsen GT 

PROVIDER: S-EPMC2504012 | biostudies-literature | 2007 May

REPOSITORIES: biostudies-literature

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Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

Halvorsen Geoff T GT   Roush William R WR  

Organic letters 20070505 11

The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions. ...[more]

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