In this communication, a chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction of unmodified Morita-Baylis-Hillman alcohols with azomethine imines has been achieved through a kinetic resolution of MBH alcohols under mild conditions, giving pharmaceutically interesting functionalized hetero-bicyclo[3.3.1]nonane derivatives in good to excellent yields with excellent enantioselectivities.
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http://dx.doi.org/10.1039/c9cc05483a | DOI Listing |
Org Biomol Chem
September 2024
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Org Lett
July 2024
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal-462066, India.
Spirooxazines represent a privileged heterocyclic scaffold having pronounced biological importance. Herein, we introduce a chiral bifunctional squaramide catalyzed highly chemoselective cascade reaction involving aza-Michael/1,2-addition/oxa-Michael addition of -substituted hydroxylamine with keto-bis-enones. This strategy enables the synthesis of highly enantioenriched oxa-spirooxazines with a broad substrate tolerance.
View Article and Find Full Text PDFRSC Adv
June 2024
College of Pharmacy, Guangxi Zhuang Yao Medicine Center of Engineering and Technology, Guangxi University of Chinese Medicine Nanning Guangxi 530200 P. R. of China
Bifunctional chiral squaramide-catalyzed highly enantioselective Michael addition of nitromethane to diverse 2-enoylazaarenes was successfully performed. This protocol provided a set of chiral azaarene-containing γ-nitroketones with up to 98% yield and 98% ee in a solvent-free catalytic system under mild conditions. Furthermore, gram-scale synthetic utility was also showcased.
View Article and Find Full Text PDFAdv Sci (Weinh)
July 2024
Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing Key Laboratory of Soft-Matter Material Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
Axially chiral thioethers and sulfoxides emerge as two pivotal classes of ligands and organocatalysts, which have remarkable features in the stereoinduction of various asymmetric transformations. However, the lack of easy methods to access such molecules with diverse structures has hampered their broader utilization. Herein, an oxidative kinetic resolution for sulfides using a chiral bifunctional squaramide as the catalyst with cumene hydroperoxide as the terminal oxidant is established.
View Article and Find Full Text PDFJ Org Chem
January 2024
Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Chiral diarylmethylamides are a privileged skeleton in many bioactive molecules. However, the enantioselective synthesis of such molecules remains a long-standing challenge in organic synthesis. Herein, we report a chiral bifunctional squaramide catalyzed asymmetric aza-Michael addition of amides to generated -quinomethanes, affording enantioenriched diarylmethylamides in good yields with excellent enantioselectivities.
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