Trimethylsilyl Methanenitronate

Chemistry of N,N-Bis(silyloxy)enamines. 3. N,N-Bis(silyloxy)enamines as β-C-Nucleophiles in Reaction with Acetals Mediated by Trimethylsilyl Trifluoromethanesulfonate1

“…Silylation of nitro compounds may afford silyl derivatives of two different types, namely, silyl nitronates and N,N - b is(silyloxy) ena mines (BENA). Whereas thoroughly studied transformations of silyl nitronates constitute a substantial part of the chemistry of aliphatic nitro compounds, the reactivity of BENA remains scarcely investigated . At the same time, these derivatives may become attractive intermediates in organic synthesis, especially in light of the convenience of their preparation and handling …”

ChemInform Abstract: Structure and Reactivity of Five‐ and Six‐Ring N,N‐, N,O‐, and O,O‐ Acetals: A Lesson in Allylic 1,3‐Strain (A1,3 Strain).

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The X-ray structures of fifteen 1,3-imidazolidine, 1,3-oxazolidine, 1,3-dioxan-4-one, and hydropyrimidine-4( I H)-one derivatives are described ( Table 2) and compared with known structures of similar compounds (Figs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. The differences between structures containing exocyclic N-acyl groups and those lacking this structural element arise from the A',' effect of the amide moieties.

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“…cis-Disubstituted oxazolidinone 9 (from methionine and pivalaldehyde; CSD: FENJEN)[57]. The enolate of 9 was used to prepare c( -branched methionines in enantiomerically pure form [l][12] The enolate of 9 was used to prepare c( -branched methionines in enantiomerically pure form [l][12] …”