Methoxymethyl bis trimethylsilyl amine

Aldol and Aldol-type Reactions. Yamamoto also used this procedure for the aldol reaction between TMS enol ethers with aldehydes and ketones (eq 7).  

The use of TMS-enol ethers, and -ketene acetals with the TMSNTf2 catalyst was also shown to be quite effective for the a-amido alkylation (eq 8). High diastereoselectivty was obtained in many cases, whereas TfOH was again unable to promote the reaction. 

Tetrahydropyran Formation. The use of an appropriately substituted allylsilane with a variety of electrophiles with 10% TMSNTf2 gave the cyclized tetrahydropyran compounds (eq 9). For this reaction, TMSNTf2 outperformed a variety of Lewis acids including TMSOTf, TiCLj, TiCl2(0/-Pr)2, SnCU, BF3-OEt2, and EtAlCl2.i  

Takasu, K. Hosokawa, N. Inanaga, K. Ihara, M., Tetrahedron Lett. 2006, 47,6053. 

Kuhnert, N. Peverley, J. Robertson, J., Tetrahedron Lett. 1998,39,3215. Ishihara, K. Hiraiwa, Y. Yamamoto, H., Synlett IWtl, 1851. 

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Amines (S)-1 -Amino-2-methoxymethyl-1 -pyrrolidine. Azidomethyl phenyl sulfide. Bis(methoxycarbonyl)sulfur diimide. N,N-Bis(trimethylsilyl)rnethoxymethylamine. 

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