Abstract
In this paper, the organocatalytic asymmetric 1,4-Michael addition reaction of azadienes and α-thiocyanoindanones was investigated. A series of chiral benzofuran compounds containing thiocyano group and quaternary carbon center were synthesized in moderate yields with good enantioselectivities (up to 90:10 er) and high diastereoselectivities (up to >95:5 dr). This is the first case of 1,4-Michael addition reaction using α-thiocyanoindanones to obtain a series of chiral thiocyano compounds and further broaden the scope of application of azadiene substrates. In addition, a possible reaction mechanism is also described in the article.
Highlights
Benzofuran derivatives are an important class of heterocyclic compounds in many biologically active natural products [1,2,3,4]
As far as we know, azadienes derived from benzofurans can undergo 1,4Michael addition reactions with suitable nucleophiles due to their high reactivity to quickly construct multisubstituted benzofuran derivatives, and a variety of benzofuran derivatives have been successfully obtained by using azadienes [9,10,11,12,13,14]
A series of organic catalysts were used to select the optimal catalyst for the 1,4-Michael addition reaction between azadienes and α-thiocyanoindanones
Summary
Benzofuran derivatives are an important class of heterocyclic compounds in many biologically active natural products [1,2,3,4]. Compounds containing benzofuran structural motifs exhibit excellent anticancer, antioxidation, and antifungal activities, and they can be used as important structural motifs for some organic materials and drug molecules (Figure 1) [5,6,7,8]. The development of efficient and convenient ways to obtain compounds containing benzofuran structural motifs is the common goal pursued by many organic chemists. As far as we know, azadienes derived from benzofurans can undergo 1,4Michael addition reactions with suitable nucleophiles due to their high reactivity to quickly construct multisubstituted benzofuran derivatives, and a variety of benzofuran derivatives have been successfully obtained by using azadienes [9,10,11,12,13,14].
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