Kampen Daniela, Reisinger Corinna M, List Benjamin
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
Top Curr Chem. 2010;291:395-456. doi: 10.1007/978-3-642-02815-1_1.
Chiral Brønsted acid catalysis is an emerging area of organocatalysis. Since the pioneering studies of the groups of Akiyama and Terada in 2004 on the use of chiral BINOL phosphates as powerful Brønsted acid catalysts in asymmetric Mannich-type reactions, numerous catalytic asymmetric transformations involving imine activation have been realized by means of this catalyst class, including among others Friedel-Crafts, Pictet-Spengler, Strecker, cycloaddition reactions, transfer hydrogenations, and reductive aminations. More recently, chiral BINOL phosphates found application in multicomponent and cascade reactions as for example in an asymmetric version of the Biginelli reaction. With the introduction of chiral BINOL-derived N-triflyl phosphoramides in 2006, asymmetric Brønsted acid catalysis is no longer restricted to reactive substrates. Also certain carbonyl compounds can be activated through these stronger Brønsted acid catalysts. In dealing with sensitive substrate classes, chiral dicarboxylic acids proved of particular value.
手性布朗斯特酸催化是有机催化领域一个新兴的研究方向。自2004年秋山和寺田课题组率先研究将手性联萘酚磷酸酯用作不对称曼尼希型反应中高效的布朗斯特酸催化剂以来，借助这类催化剂已实现了众多涉及亚胺活化的催化不对称转化反应，其中包括傅克反应、皮克特-施彭格勒反应、斯特雷克反应、环加成反应、转移氢化反应及还原胺化反应等。最近，手性联萘酚磷酸酯在多组分反应和串联反应中得到了应用，比如在不对称的大inelli反应中。随着2006年手性联萘酚衍生的N-三氟甲磺酰基磷酰胺的引入，不对称布朗斯特酸催化不再局限于活性底物。某些羰基化合物也能通过这些更强的布朗斯特酸催化剂实现活化。在处理敏感底物类型时，手性二羧酸被证明具有特殊价值。
