Читать книгу Catalytic Asymmetric Synthesis - Группа авторов - Страница 46

The advent of chiral Brønsted acids in the early 2000s followed extensive studies on chiral Lewis acid catalysts [1]. While a range of compounds can be considered chiral Brønsted acids (Figure 2.1) [2], including thiourea 1 [3], 2 [4], TADDOL (α,α,α′,α′‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol) 3 [5], 1,1′‐bi‐2‐naphthol (BINOL) derivatives 4 [6], and bis‐quinoline acid salt (HQuin‐BAM) 5 [7], we will primarily focus on more acidic BINOL‐derived phosphorus‐ and sulfur‐containing organic acids, such as phosphoric acid (CPA [chiral phosphoric acid]) 6 [8, 9], dicarboxylic acid 7 [10], disulfonic acid (BINSA) 8 [11], disulfonimide (DSI) 9 [12], imidodiphosphate (IDP) 10 [13], and imidodiphosphorimidate (IDPi) 11 [13]. This chapter will provide a compilation of transformations that have been mediated by chiral Brønsted acids [15, 16], and is organized by the type of reactions starting from nucleophilic reaction, cycloaddition reaction, Michael reaction, reduction, addition to alkenes, substitution, rearrangements, and others.