Abstract
[GRAPHICS] MeSO3H effects the intramolecular allenylation of a series of aldehydes I to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol, 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.
Original language | English |
---|---|
Pages (from-to) | 1631-1634 |
Number of pages | 4 |
Journal | The Journal of Organic Chemistry |
Volume | 73 |
Issue number | 4 |
DOIs | |
Publication status | Published - 1 Jan 2008 |