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21.14.1.2.4 Method 4: Organometallic Additions to Acylphosphonates

DOI: 10.1055/sos-SD-021-00911

Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R., Science of Synthesis, (2005) 21, 918.

Nucleophilic addition to carbonyl groups has provided an effective way to generate new C—C bonds. Acylphosphonates possess a carbonyl group that is activated for nucleophilic attack. When Grignard reagents or indium-mediated reactions are employed, there is preference for nucleophilic attack at the carbonyl position over the phosphoryl position.

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