TBAF-Triggered Aldol-Type Addition of α-Triethylsilyl-α-diazoacetone.

Imen Abid, Pascal Gosselin, Monique Mathé-Allainmat, Souhir Abid, Gilles Dujardin, Catherine Gaulon-Nourry

The Journal of organic chemistry 2015 Oct 16

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Aldol-type addition of α-triethylsilyl-α-diazoacetone was achieved under nucleophilic activation by tetrabutylammonium fluoride (TBAF). The use of a semistoichiometric amount of TBAF (protocol P1) provided the corresponding β-hydroxy-α-diazoacetone as the sole product. Alternatively, the use of a catalytic amount of TBAF led to a mixture of β-hydroxy- and β-silyloxy-α-diazoacetone products, which was cleanly desilylated with Et3N·3HF (protocol P2). The weakly basic conditions employed tolerate a wide range of substrates and constitute a high-yielding, convenient complementary procedure to the low-temperature LDA-promoted aldol-type addition of diazoacetone.

Citation

Imen Abid, Pascal Gosselin, Monique Mathé-Allainmat, Souhir Abid, Gilles Dujardin, Catherine Gaulon-Nourry. TBAF-Triggered Aldol-Type Addition of α-Triethylsilyl-α-diazoacetone. The Journal of organic chemistry. 2015 Oct 16;80(20):9980-8