Divergent Asymmetric Reactions of ortho-Quinone Methides with α-Thiocyanato Indanones for the Synthesis of Spiro- and Fused-Indanones was written by Liu, Xianghui;Wang, Kai;Liu, Yan;Li, Can. And the article was included in Chemistry – A European Journal in 2021.COA of Formula: C32H28F6N4O3 This article mentions the following:
Reported in this work is a water triggered chemo-divergent enantioselective spiro-annulation and cascade reaction of ortho-quinone methides (o-QMs) with α-thiocyanato indanones catalyzed by a chiral organic base. In the case of spiro-annulation, the use of trace amount of water as additive is critical to achieve high enantioselectivity (up to 96% ee). We found that a cascade reaction was enabled by just tuning the ratio of water in solvent. Accordingly, two new highly efficient asym. reactions for the divergent synthesis of spiro- and fused-indanone scaffolds, i.e., I and II, with excellent enantioselectivities (up to 99% ee) were developed. Mechanistic investigations suggest that interfacial hydrogen bonding may play an important role in achieving the switchable reaction pathways. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0COA of Formula: C32H28F6N4O3).
3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.COA of Formula: C32H28F6N4O3
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider