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Lewis Acid Induced α-Alkylation of Carbonyl CompoundsNew synthetic methods (35) (1982)

Reetz, Manfred T.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 21 (1982), S. 96-108

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ISSN: 0570-0833

Keywords: Lewis acids ; Alkylation ; Carbonyl compounds ; Synthetic methods ; Silyl enol ethers ; C-C coupling ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Carbonyl compounds undergo α-alkylation via the corresponding silyl enol ethers using SN1 active alkyl halides or acetates in the presence of Lewis acids. This methodology extends the scope of carbonyl chemistry considerably, since SN1 active alkylating agents are generally base sensitive and therefore unsuitable for reactions with enolate anions or nitrogen analogs. A prime example is the α-tert-alkylation of aldehydes, ketones and esters.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.198200961

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