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Please login to access the full content or check if you have access via23.14.1.1.7.3 Variation 3: Microwave-Enhanced Wolff Rearrangement
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Tidwell, T. T., Science of Synthesis, (2006) 23, 587.
The microwave-enhanced Wolff rearrangement of amino acid derived diazo ketones 104, with capture of the derived ketenes 105 by imines 106, provides a route to the β-lactams 107A and 107B (Scheme 33).[90] The diastereomeric ratios of the product are 2:1 for R1 = Me and 9:1 for R1 = t-Bu. Microwaves also enhance the Wolff rearrangement of other ketene precursors, such as 1-diazotridecan-2-one.[91] The electric field from microwave irradiation may affect the conformational preference of the diazo ketones and thereby enhance the efficiency of the Wolff rearrangement.[91]
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References
| [90] | Meeeee, M. M.; Meeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [91] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeeeeee, M. M. M.; Mee, M.; Meee, M. M.; Meeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
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