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4.4.40.64 Method 64: Aziridination and Ring Opening

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024911.

β,γ-Unsaturated amino acids, noted for their pharmacological properties, can be made by aziridination of allylsilanes followed by spontaneous desilylative ring opening. For example, addition of (ethoxycarbonyl)nitrene, generated from ethyl [(4-nitrophenyl)sulfonyl]oxycarbamate, to allylsilane 260 gives β,γ-unsaturated α-amino ester derivative 261 (Scheme 104).[‌90‌] However, ester 262 under similar conditions gives a mixture of 263 and 264 (263/264 1.6:1); protodesilylation of vinylsilane 264 yields alkene 263, thereby improving the overall yield in this reaction.[‌90‌] This application took advantage of the method of synthesis of allylsilanes described in Section 4.4.40.7.3.

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