Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 6, Pages 4825-4834Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02854
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Funding
- National Natural Science Foundation of China [21571144]
- Zhejiang Provincial Natural Science Foundation of China [LY18B020011, LQ19B020004]
- Foundation of Zhejiang Educational Committee [Y201839490]
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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.
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.
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