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. Author manuscript; available in PMC: 2023 Jun 8.
Published in final edited form as: J Am Chem Soc. 2020 Aug 10;142(33):14201–14209. doi: 10.1021/jacs.0c04994

Figure 3.

Figure 3.

Asymmetric alkylation of selenazoline under photoredox conditions and their derivatization. (A) Scope of the β-selenolated amino acids. Deprotection conditions: (a) (1) LiOH (10.0 equiv), H2O/MeOH (1/3 v/v), 25 °C, 6 h, (2) 6 N HCl in dioxane, 50 °C, 8 h; (b) (1) LiOH (10.0 equiv), H2O/MeOH (1/3 v/v), 25 °C, 6 h, (2) 6 N HCl in dioxane, 50 °C, 8 h, (3) (Boc)2O (1.0 equiv), THF/H2O (10/1 v/v), DIPEA (2.0 equiv), 25 °C, 1 h; (c) (1) LiOH (10.0 equiv), H2O/MeOH (1/3 v/v), 25 °C, 6 h, (2) 6 N HCl in dioxane, 50 °C, 8 h, (3) N N′-bis-Boc-1-guanylpyrazole (1.0 equiv), DIPEA (2.0 equiv), MeOH, 25 °C, 3 h. (B) Absolute configuration of 3d as confirmed by X-ray crystallography. Legend: (i) diastereoselectivity determined by GC analysis of the crude reaction mixture; (ii) brsm, based on recovered starting material; (iii) mixture of diastereomers found.