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Please login to access the full content or check if you have access via Variation 3: Microwave-Enhanced Wolff Rearrangement

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623587.

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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