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When 4 Å MS was not used to remove water that might be present in the reaction mixture, an amount of p-methoxylbenzaldehyde was observed by TLC
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When 4 Å MS was not used to remove water that might be present in the reaction mixture, an amount of p-methoxylbenzaldehyde was observed by TLC
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and ref 4d. For a recent synthesis of centrolobine via the Prins cyclization, see
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Allyl transfer processes can lead to a loss in optical activity for Prins cyclization reactions (see the mechanism below). Racemization relies on the presence of water. Direct Prins cyclizations utilizing homoallylic alcohols and aldehydes generate water upon condensation. Segment-coupling Prins cyclizations developed by Rychnovsky's group, however, do not generate water in situ and therefore can be used to avoid racemization.
-
Allyl transfer processes can lead to a loss in optical activity for Prins cyclization reactions (see the mechanism below). Racemization relies on the presence of water. Direct Prins cyclizations utilizing homoallylic alcohols and aldehydes generate water upon condensation. Segment-coupling Prins cyclizations developed by Rychnovsky's group, however, do not generate water in situ and therefore can be used to avoid racemization.
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