Catalytic asymmetric synthetic method for chiral spirodiol derivative

Abstract

The invention belongs to the field of organic synthesis, and discloses a catalytic asymmetric synthetic method for a chiral spirodiol derivative. The catalytic asymmetric synthetic method comprises the following step: with chiral phosphoric acid as a catalyst, subjecting a compound as shown in a formula I in the specification and / or a compound as shown in a formula II in the specification to a reaction so as to obtain a product. In the formula I and the formula II, R1, R2, R4, R5, R6 and R7 are independently selected from any groups; and R3 is an alkyl group. The catalytic asymmetric synthetic method is a convenient, rapid and direct method for construction of a chiral spirodiol structure. The synthetic method provided by the invention has the advantages of high yield, good enantioselectivity, capability of tolerating a variety of functional groups, etc., can reduce the usage amount of the catalyst to 0.1 mol% during large-scale synthesis, and has application values in industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a catalytic asymmetric synthesis method of chiral spirocyclic diphenol derivatives. Background technique [0002] Axichiral compounds have a wide range of applications in bioactive compounds, materials, organocatalysts, and ligands. Therefore, the asymmetric construction of axial chiral compounds has always been a research hotspot, and great progress has been made. Among the well-known structures in the art, axial chiral BINOL, BINAP and other biaryl derivatives have been widely used as chiral ligands / catalysts. Due to the importance of these structures, the catalytic asymmetric configuration of biaryl derivatives has been intensively studied, which can be achieved through stereoselective oxidation / crosslinking of two aryl substrates, asymmetrically controlled formation of The selective functionalization of aromatic compounds and other ways to obtain. [0003] Axial chiral 1,1...

AI Technical Summary

Problems solved by technology

[0003] Axial chiral 1,1'-spirodihydroindane-7,7'-diol (SPINOL for short) is a 1,1'-spirobiindane-containing compound widely used in asymmetric synthesis in recent years. The most basic and important structures of the chiral ligands (such as FuP, SDP, SpiroPAP, SPIDAM, SIPHOX, SpiroBOX, SCp, SITCP and CPA) of the backbone, but the asymmetric synthesis of SPINOL still lacks an effective way

At present, only a few studies have been involved in this field. Birman et al. first synthesized it by using a classical resolution strategy; in 2002, Zhou Qilin et al. developed a more practical method by using cinchodine chloride as a resolution reagent; recently , Zhao Yu et al. realized the kinetic resolution of SPINOL by enantioselective acylation catalyzed by N-heterocyclic carbene, however, this method only used one substrate, the ee value was lower than 50%, and the selection factor was 3.4

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