AI Article Synopsis
- The research details the process of introducing an allyl group into a specific position of a benzopyran compound using Birch reduction and enolate trapping.
- An unexpected change in the molecular conformation was observed during the reaction, leading to the introduction of the allyl group.
- Two distinct diastereomeric compounds were synthesized, both containing the allyl group in the same angular position, and were achieved in optically pure forms.
Article Abstract
The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initially formed one. Two diastereomeric Wieland-Miescher type compounds, having the allyl group at the angular position, were synthesized as optically pure forms.
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| http://dx.doi.org/10.1248/cpb.53.207 | DOI Listing |
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