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

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 c...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-10, Vol.80 (20), p.9980-9988
Main Authors: Abid, Imen, Gosselin, Pascal, Mathé-Allainmat, Monique, Abid, Souhir, Dujardin, Gilles, Gaulon-Nourry, Catherine
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Azo Compounds - chemistry
Chemical Sciences
Molecular Structure
Organosilicon Compounds - chemistry
Quaternary Ammonium Compounds - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01554