An organocatalyzed transformation to elongate unprotected carbohydrates is described. This operationally simple methodology is based on a Knoevenagel-oxa-Michael cascade. This reaction is catalyzed by proline and DBU. Products were obtained with exceptional high degrees of stereoselectivity.
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http://dx.doi.org/10.1039/c3cc48120d | DOI Listing |
Org Lett
October 2024
Department of Applied Chemistry, Anhui Province Engineering Laboratory for Green Pesticide Development and Application, and Anhui Province Key Laboratory of Crop Integrated Pest Management, Anhui Agricultural University, 230036 Hefei, China.
An intramolecular organocatalytic cascade dearomatizing spirocycloaddition reaction of indole-ynone compounds containing -silyl-naphthol substituents has been developed with the use of a chiral bifunctional thiourea. This process was able to provide various structurally diverse polycyclic spiroindolines in high yields (up to 98%) with excellent stereoselectivities (>20:1 dr, up to 98% ee) involving the formation of carbonylvinylidene -quinone methide intermediates.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2024
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal, 462066, India.
Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable and challenging task in synthetic endeavors due to their intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2-addition followed by an oxa-Michael addition cascade in a high atom and step economical pathway.
View Article and Find Full Text PDFChem Sci
March 2024
Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology Guangming Advanced Research Institute, Southern University of Science and Technology (SUSTech) Shenzhen 518055 China
Compared with well-developed construction of C-C atropisomers, the synthesis of C-N atropisomers remains in its infancy, which is recognized as both appealing and challenging. Herein, we achieved the first organocatalyzed asymmetric synthesis of C-N atropisomers by formal C-O amination. With the aid of a suitable acid, 3-alkynyl-3-hydroxyisoindolinones reacted smoothly with 1-methylnaphthalen-2-ols to afford a wide range of atropisomers by selective formation of the C-N axis.
View Article and Find Full Text PDFOrg Lett
February 2024
Key Laboratory of Chemistry in Ethnic Medicinal Resources, School of Ethnic Medicine, Yunnan Minzu University Kunming, 650500, China.
The direct functionalization of β-C(sp)-H bonds in enamides has garnered increasing attention within the realm of organic synthesis. However, these remarkable advancements are predominantly dependent on transition metals; limited success has been achieved via organocatalytic catalysis. Herein, we report a CPA-catalyzed β-C(sp)-H functionalization of enamides cascade intramolecular cyclization to synthesize the chiral dihydropyrimido[1,6-]indoles bearing -difluoromethylene.
View Article and Find Full Text PDFBeilstein J Org Chem
August 2023
Department of Physical and Chemical Sciences, Università degli Studi dell'Aquila, via Vetoio, 67100, L'Aquila, Italy.
Asymmetric organocatalyzed multicomponent reactions represent an important toolbox in the field of organic synthesis to build complex scaffolds starting from simple starting materials. The Enders three-component cascade reaction was a cornerstone in the field and a plethora of organocatalyzed cascade reactions followed. However, acetaldehyde was not shown as a successful reaction partner, probably because of its high reactivity.
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