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4.4.15 Product Subclass 15: Silyl Imidic Esters (Silylimino Ethers)

DOI: 10.1055/sos-SD-004-00329

Lukevics, E.; Pudova, O.Science of Synthesis, (20024305.

Silyl imidic esters (or silylimino ethers), compounds containing the SiOC=N fragment, are useful reagents for organic synthesis and have been described extensively.[‌1‌‌4‌] The simple and commercially available O,N-bis(trimethylsilyl)acetamide [trimethylsilyl N-(trimethylsilyl)acetimidate], MeC(OTMS)=NTMS, and O,N-bis(trimethylsilyl)trifluoroacetamide, F3CC(OTMS)=NTMS,[‌1‌,‌2‌] are among the most powerful reagents for the introduction of trimethylsilyl groups for the efficient protection of heteroatoms and for activation or modification of other functionalities.[‌3‌,‌4‌] Silyl ethers of pyrimidine (uracil, thymine, cytosine), purine, and other heterocyclic bases are very important intermediates for preparation of nucleosides by subsequent glycosylation.[‌5‌]

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