0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. 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

Meeeee 888 Meeeeeeeeee ee β,γ-Meeeeeeeeee α-Meeee Meeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

β,γ-Meeeeeeeeee α-Meeee Meeee Meeeeeeeeee 888 eee 888; Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee eeeeeeeeeee 888 (888ee, 8.8eeee) ee MM8Me8 (8eM) ee ee, MeM eee 8-M8MM8M8MM8MMMM8Me eeee eeeee eeeeeeeeeee [eeeee eeeee (eeeeeeeee/8-M8MM8M8MM8MMMM8Me/MeM) 8:8:8]. Mee eeeeeee eee eeeeeee eee 88e, MM8Me8 (88eM) eee eeeeee (888eM) eee eeeee. Meeee eeeeeeeeee, eee eeeeee eeeee eee eeeeeeeeeeee ee eeeee. Mee eeeeeeee eeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); α-eeeee eeeeee 888 eee 888 eeee eeeeeeeee eeeeeeeeee; eeeee ee 888: 888ee (88%); eeeee ee 888: 888ee (88%).