Also known as Boc. Used extensively in amine protection. Stable towards most nucleophiles and bases. Easily get rid of under TFA/CH2Cl2 (1/1). Reduced to methyl group under LAH to make single methyl substitution. Applied for synthesis of of highly enantiomerically enriched N-Boc protected amino alcohols by aminohydroxylating a variety of substituted styrenes,1 Pd-catalyzed cross-coupling reaction with various aryl(Het) halides,2 one-pot transformation into amides in acy halide-methanol mixtures.3,4
1. Tetrahedron Lett. 1998, 39, 4099.
2. Tetrahedron Lett. 2010, 51, 4445.
3. Synthesis, 2002, 203.
4. Synlett 2000, 635.