Indole-based chiral heterocycles constitute a class of important heterocyclic compounds that are found in numerous natural products, pharmaceuticals, pesticide, and functional materials. The efficient and highly enantioselective synthesis of chiral indole derivatives has become one of the most important issues in organic chemistry. Due to the simple reactivity of the traditional indoles, their involved catalytic asymmetric reactions are very limited, resulting in the limited types of constructed indole-based frameworks. To solve these challenging issues, chemists devised a strategy of introducing simple functional groups to the indole ring, so as to obtain a series of functionalized indole derivatives, namely indole-based platform molecules, as efficient building blocks for constructing chiral indole-related frameworks. Among them, 2-indolylmethanols are a class of important platform molecules, which were designed on the consideration that the introduction of a hydroxymethyl group to C2-position of the indole ring would change the reactivity and the reactive site of the indole ring. This class of platform molecules can act as either electrophiles or nucleophiles, and can act as multi-carbon building blocks in catalytic asymmetric reactions. Therefore, the design and development of 2-indolylmethanols as platform molecules have provided a new strategy for the efficient and highly enantioselective synthesis of chiral indole derivatives. The advances in catalytic asymmetric reactions using 2-indolylmethanols as platform molecules are summarized, which will open a new window for designing and application of new types of indole-based platform molecules.

Key words: chiral indole chemistry, catalytic asymmetric reaction, platform molecule, indolylmethanol