Pentaerythritol loaded chiral diamine derivative thiourea catalyst, preparation method and application thereof

Abstract

The invention discloses a pentaerythritol loaded chiral diamine derivative thiourea catalyst, a preparation method and an application thereof. The structure thereof is as shown in a formula (I). The preparation method of the pentaerythritol loaded chiral diamine derivative thiourea catalyst comprises the following steps: a) reacting S,S-N-Boc-cyclohexanediamine with CH3I under room temperature in the presence of acetonitrile and K2CO3 and then reacting with Br(CH2)nBr, thereby acquiring an intermediate (1); b) reacting the intermediate (1) with F3CCO2H, thereby acquiring an intermediate (2); c) reacting the intermediate (2) with 3,5-bi(trifluoromethyl) isothiocyanate under room temperature, acquiring an intermediate (3); and d) reacting the intermediate (3) with pentaerythritol under the existence of alkali and phase transfer catalyst, thereby acquiring the pentaerythritol loaded chiral diamine derivative thiourea catalyst shown as formula (I). The pentaerythritol loaded chiral diamine derivative thiourea catalyst can be applied to the dissymmetric Michael addition reaction. The pentaerythritol loaded chiral diamine derivative thiourea catalyst can be simply separated and purified and can be reused.

Description

technical field [0001] The invention relates to the field of catalytic organic synthesis, in particular to a pentaerythritol immobilized chiral diamine-derived thiourea catalyst and a preparation method and application thereof. Background technique [0002] The Michael addition reaction is one of the important methods for the formation of new carbon-carbon bonds by the conjugated addition of nucleophiles to α,β unsaturated carbonyl compounds, and plays an important role in the formation of asymmetric C-C bonds. In recent years, with the emergence of chiral catalysts, asymmetric Michael addition reactions have been developed rapidly. Studies have shown that chiral diamine-derived thiourea catalysts can well catalyze asymmetric Michael addition reactions. It can interact with the substrate charge acceptor molecule α,β -The carbonyl or nitro group of the unsaturated compound forms a double hydrogen bond, which improves the electrophilic performance of the acceptor. The terti...

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Problems solved by technology

However, the thiourea catalyst derived from chiral diamine is expensive, difficult to separate from the product, and difficult to recycle. Therefore, under the premise of ensuring its catalytic activity, immobilizing it on a suitable carrier is the solution to catalyst recovery and recycling. Effective Ways

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