A new class of structurally rigid tricyclic amphibian chiral catalyst was rationally designed based on the hexahydropyrrolo[2,3-b]indole skeleton as a new type of chemzyme. This new type of chemzyme possesses a structurally rigid tricyclic skeleton and a chiral pocket which provides a well-organized chiral environment for asymmetric induction, as well as a hydrophobic pocket to enable organocatalytic reactions to proceed smoothly both in organic solvents and in water.
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