Gamma-alkenyl substituted butenolide or butenolactam compound and asymmetric synthesis method and ligand of gamma-alkenyl substituted butenolide or butenolactam compound

Abstract

The invention discloses an asymmetric synthesis method of a gamma-alkenyl substituted butenolide or butenolactam compound. The method adopts cheap nickel to catalyze a [3+2] asymmetric cycloaddition reaction of a cyclopropenone compound and alpha, beta-unsaturated ketone or imine, the selective insertion reaction of intermolecular C=X after nickel-catalyzed C-C bond activation is realized for thefirst time, wherein X is equal to O or N, the gamma-alkenyl substituted butenolide or butenolactam compound is obtained in a high yield, high enantioselectivity and chirality controllable manner, thesynthesis method is novel, condition mildness, substrate with good applicability, simple and efficient reaction, cheap and readily available catalyst, according to the present invention, the synthesisprocess is simple, the atom economy is good, the synthesis product is easy to derivatize, the method can be widely used in completely-synthesized designed synthesis building blocks and new chiral drug derivatives, and the ligand compound is further provided, and can be used for the asymmetric synthesis of gamma-alkenyl substituted butenolide or butenolactam compounds.

Description

[0001] Cross References to Related Applications [0002] This application claims the priority of the Chinese patent application CN201910727718.3 submitted on August 8, 2019, the content of which is hereby incorporated into this application. technical field [0003] The invention relates to a γ-alkenyl substituted butenolactone or butenolactam compound and a synthesis method thereof, belonging to the technical field of chemical synthesis. Background technique [0004] Transition metal-catalyzed asymmetric carbon-carbon (C-C) bond activation is a powerful tool to realize the construction and transformation of new complex molecules. In the prior art, it is mainly realized by low-priced noble metals (TMs, such as Rh, Pd, Ir, etc.), nickel Ni It is a more abundant and cheaper metal catalyst for C-C activation, but there are few reports, and it mainly focuses on the field of intramolecular reactions. The insertion and reductive elimination reaction of polar unsaturated bonds (suc...

AI Technical Summary

Problems solved by technology

[0008] Therefore, it is of potential application value and important to develop an intermolecular coupling reaction based on C-C bond activation realized by cheap metals, and to realize efficient and selective construction of complex molecules. Methodological significance, but also full of challenges

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