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21.14.1.2.8 Method 8: Reaction of Acylphosphonates with Phosphorus(III) Compounds

DOI: 10.1055/sos-SD-021-00911

Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R.Science of Synthesis, (200521925.

Acylphosphonates can undergo nucleophilic addition with trialkyl phosphites. As noted in Section 21.14.1.2.4, nucleophilic attack occurs preferentially at the carbonyl position of acylphosphonates. After initial nucleophilic attack, a number of intermediates can be formed depending on the method and type of acylphosphonate system used. These intermediates include anionic and carbene-like intermediates that subsequently undergo cyclization.


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