Asymmetric Construction of α-Substituted β-Hydroxy Lactones via Ni Catalyzed Decarboxylative Addition Reaction

We described a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction of 2-oxotetrahydrofuran-3-carboxylic acid/2-oxochromane-3-carboxylic acid derivatives with different kinds of carbonyls. Under optimal reaction conditions, alpha-substituted beta-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter have been generated with high levels of functional-group compatibility. Furthermore, proficient transformations of products were also described, in which an aliphatic tertiary alcohol and a multi-substituted 1,4-diol were smoothly constructed through hydrogenation and ring-opening reaction, respectively.

Automated summary

In this study, a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction was described, yielding alpha-substituted beta-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter. Successful transformations of the products into an aliphatic tertiary alcohol and a multi-substituted 1,4-diol were also achieved. This research has significant theoretical and practical implications.