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Please login to access the full content or check if you have access via23.14.1.2.2.5 Variation 5: γ-Lactams by Intramolecular Cyclization of Monoalkylketenes with Nitrogen Nucleophiles
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Tidwell, T. T., Science of Synthesis, (2006) 23, 597.
Photochemical Wolff rearrangement of the diazo ketone 160 (R1 = CO2Me; R2 = H) gives the proline precursor 162 via an intermediate ketene 161 in “good” yield (Scheme 50).[110] Cyclization of diazo ketones 160 (R2 = Ts) occurs through a silver benzoate induced thermal Wolff rearrangement in tetrahydrofuran to form the corresponding pyrrolidinones 162 (Scheme 50).[111] When this rearrangement is conducted in methanol, the pyrrolidinone is the sole product from 160 (R1 = Me, Bn), whereas the methyl ester, formed through capture of the ketene, is the major or exclusive product from 160 (R1 = H, CH2CH2SMe).[111]
Meeeee 88 Meeeeeeee ee γ-Meeeeee ee Meeeeeeeeeeeee Meeeeeeeeee ee Meeeeeeeeeee eeee Meeee Meeeeeeeeeeeee[888,888]
Meeeeeeeee ee eee β-eeeee eeee eeeeeee eeeee eeeeeee 888 eeeee eee eeeeeeeeeeeee eeeeeee 888 eeee eeeeeee ee eeee eee γ-eeeeeee 888 (Meeeee 88).[888]
Meeeee 88 γ-Meeeeee eeee Meeee Meeeeeeeeeeee eee Meeeee Meeeeeeeeee[888]
| M8 | M8 | Meeeeeee Meeeee ee M8 eee M8 ee 888 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|---|
| eMe | Me | eee | Mee | 88 | [888] |
| eMe | Me | eee | MM8Me | 88 | [888] |
| eMe | Me | eeeee | Mee | 88 | [888] |
| eMe | Me | eeeee | MM8Me | 88 | [888] |
| Me | Me | eee | Mee | 88 | [888] |
| MMe | 8-MeMM8M8 | eee | Mee | 88 | [888] |
| eMe | (MM8)8Me | eee | Mee | 88 | [888] |
| MMe | 8-MeMM8M8 | eeeee | Mee | 88 | [888] |
References
| [110] | Meeeeeeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [111] | Meee, M.; Mee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [112] | Me, M.-M.; Meee, M.; Meeee, M.-M.; Mee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
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