Aminocarboxylic acid silyl

Trimethylchlorosilane/triethylamine Isocyanatocarboxylic acid silyl esters from aminocarboxylic acids via aminocarboxylic acid silyl ester hydrochlorides and carbophenoxyaminocarboxylic acid silyl esters... 

Without additional reagents Aminocarboxylic acid silyl esters from lactones and aminosilanes... 

The most extensively studied derivatization procedures for amino acids are (a) esterification followed by acylation, and (b) cyclization of the a-aminocarboxylic acids to oxazolidinones, followed by acylation. Other significant procedures include (c) alkoxycarbonylation followed by esterification, and (d) trimethyl-silylation. Comments on all four procedures are given below... 

A soln. of startg. chiral lactone in abs. ethanol treated with N-cyclohexylhydroxyl-amine at room temp, for 3 h, the solvent removed, the mixture chromatographed, and the adduct silylated by standard procedure - (3S)-product. Y 73%. The products are readily converted to chiral P-aminocarboxylic acids. F.e.s. I. Panfil et al.. Tetrahedron Letters 30, 1527-8 (1989). 

Aminoalcohols from oc-aminocarboxylic acids C(NH2)COOH C(NH2)CH20H via silyl esters s. 23, 82 direct reduction in the presence of methanol cf. A. K. Saund and N. K. Mathur, Indian J. Chem. 9, 936 (1971)... 

Aminations which afford 6-aminocarboxylates are of interest in relation to monobactam antibiotics. A secondary aminomethyl group can be introduced at the -position of carboxylic esters by reaction of hexahydro-1,3,5-triazines with ketene silyl acetals in the presence of a catalytic quantity of trifluoromethanesulphonic acid (Scheme 25). The triazine (10) is considered to be converted into an N-silylated methyleneiminium salt which undergoes addition of the ketene silylacetal (11). 

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