You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via3.6.12.1.1.4 (Acyloxy)allenes as All-Carbon 1,3-Dipoles
Please login to access the full content or check if you have access via
Zhang, L., Science of Synthesis Knowledge Updates, (2011) 2, 104.
In the presence of gold catalysts, allenes have been shown to behave as all-carbon 1,3-dipoles in [3 + 2][90] and [4 + 3][91,92] dipolar cycloaddition reactions. In 2010, it was reported that (acyloxy)allenes, generated via gold-catalyzed 3,3-rearrangements, can likewise be transformed into all-carbon 1,3-dipoles (e.g., 54, Scheme 37), which react with a tethered furan in a concerted [4 + 3] dipolar cycloaddition.[93] The resulting gold carbene intermediate 55 undergoes either 1,2-C–H insertion to afford an allylic acetate (e.g., 56) or acetoxy migration to afford a tricyclic enol acetates (e.g., 57). Interestingly, different catalysts show contrasting selectivities.
Meeeee 88 [8 + 8] Meeeeeeeeeeeee ee ee (Meeeeee)eeeeee[88]
| Meeeeeee | Meee (e) | Meeee (%) ee 88 | Meeee (%) ee 88 | Mee |
|---|---|---|---|---|
 |
88 | 88 | 88 | [88] |
| MeMe{8-MeM8M8M(e-Me)8}/MeMeM8 | 8 | 8 | 88 | [88] |
References
| [90] | Meeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [91] | Meeeee, M.; Móeee, M.; Meeeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeóe, M.; Meeeeeeñee, M. M., Meee.–Mee. M., (8888) 88, 8888. |
| [92] | Meeeeóe, M.; Meeeee, M. M.; Meeeáeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [93] | Meee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M., Meee.–Mee. M., (8888) 88, 888. |
Return to Top