ppm. 1,2,3-triazole ring was created by click reaction using Cu(I)-catalyzed azide/alkyne (CuAAc) cycloaddition. The azide was synthesized in situ by dissolving sodium azide in the mixture of 2-methylbenzyl chloride, trimethylamine, Furin and ideals of (+)-1 and (?)-1 were determined by a literature method [45]. The ideals for (+)-10 (92%) and AMG 487 S-enantiomer (?)-10 (98%) were determined by HPLC using Phenomenex-IA AMG 487 S-enantiomer column after derivatization with benzoyl chloride in the presence of TEA. Analytical conditions were as follows: eluent: a mixture of ideals for (?)-4 (98%), (+)-4 (95%), (?)-13 (95%) and (+)-13 (96%) were determined by GC on a Chirasil-L-Val column (25 m): 180 C isotherm, 1 mLmin?1, retention occasions (?)-13: 4.91 min, (+)-13: 4.52 min; circulation rate 1 mLmin?1, 160 C for 5 min 180 C (rate of heat rise 10 C/min; retention occasions (?)-4: 11.84 (min), (+)-4: 12.64 (min). The ideals of the domino ring closure compounds (?)-6 and (+)-6 were identified by HPLC using Chiracel-OD-H column, eluent: a mixture of ideals of the domino ring closure products (?)-15 and (+)-15 were identified by HPLC using Phenomenex-IA column, eluent: a mixture of values of the RDA products (?)-8 and (+)-8 AMG 487 S-enantiomer were determined by HPLC using Phenomenex-IA column, eluent: a mixture of values of RDA products (?)-9 and (+)-9 were determined by HPLC using ChiralPak-IA column, eluent: a mixture of = ?12.1 (c = 0.5, H2O), lit [57] = = +12.0 (c = 0.5, H2O). Lit. [58] = +13.8 (c = 1, H2O). [(?)-11]: white crystals (85% yield) m.p. 236C238 C, = ?62 (c = 0.5, H2O). [(+)-11]: white crystals (91% yield) m.p. 233C237 C, = +62 (c = 1, H2O). 1H and 13C NMR data of the enantiomeric amino acids were identical with those of the racemic compounds [55,56]. 3.2.2. Synthesis of Boc-Protected Amino Acids [(+)-3, (?)-3, (+)-12, (?)-12] To a solution of the appropriate 2-aminonorbornene carboxylic acid [(+)-2, (?)-2 (+)-11 or (?)-11, 3.1 g, 10 mmol] in 100 mL of a 2:1 dioxane/H2O mixture, 25 mL 1 M NaOH was AMG 487 S-enantiomer added. The perfect solution is was cooled to 0 C and Boc2O (2.4 g, 11 mmol) was added. The combination was stirred at 0 C for 1 h, warmed to r.t., stirred for 4 h and, finally, it was evaporated to 30 mL. AMG 487 S-enantiomer The solvent was acidified with 10% H2SO4 (pH = 2.5) and the resulting mixture was extracted with EtOAc (3 50 mL). The solvent was evaporated, and the crude product was filtered off from Et2O and recrystallized from iPr2O. [(?)-3]: white crystals (87% yield), m.p. 133C135 C, = ?78 (c = 1, EtOH). [(+)-3]: white crystals (91% yield), m.p. 136C137 C, = +76 (c = 1, EtOH). [(?)-12]: white crystals (85% yield), m.p. 132C135 C, = ?14 (c = 1, EtOH). [(+)-12]: white crystals (91% yield), m.p. 133C134 C, = +13 (c = 1, EtOH). 1H and 13C NMR data of the enantiomeric amino acids were identical with those of the racemic compounds [54,55,56,57,58,59]. 3.2.3. Synthesis of Boc-Protected Propargyl Amides [(+)-4, (?)-4, (+)-13, (?)-13] A mixture of the appropriate amino acid [(+)-3, (?)-3 (+)-12 or (?)-12, 2.53 g, 10 mmol], hydroxybenzotriazole (1.83 g, 12 mmol), [(?)-4]: White colored crystals (75% yield), m.p. 128C130 C, = ?38 (c = 1, EtOH), 1H-NMR (500 MHz, CDCl3, 30 C): = 1.42 (s, 9H, CH3) 1.60 (m, 1H, H-7), 2.10 (m, 1H, H-7), 2.20 (t, = 2.3 Hz, 1H, CCH) 2.35 (d, = 8.2 Hz, 1H, H-2), 2.69 (m, 1H, H-1), 2.98 (m, 1H, H-4), 3.85C3.92 (m, H, H-4), 4.11C4.16 (m, 1H, NCH2), 5.09C5.21.