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Article Abstract
Inherently chiral medium-ring derivatives have important applications in many research fields, such as materials science, molecular recognition, and asymmetric catalysis. However, the enantioselective assembly of these molecules, especially by organocatalytic strategies, remains a formidable challenge, and few methods are available. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) formal high-order (5 + 3) annulation of 1-(2-indolyl)naphthalen-2-ols with ynals. In the presence of an NHC pre-catalyst, base, Lewis acid and oxidant, this protocol enables the catalytic formation of C-C and C-O bonds, providing practical and facile access to an array of inherently chiral saddle-shaped eight-membered lactones featuring an oxocin-2-one scaffold with structural diversity in good efficiency and excellent enantiocontrol. Moreover, the scale-up preparation and representative late-stage transformations of the eight-membered lactones further demonstrate the application potential of this synthetic technology.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11442971 | PMC |
| http://dx.doi.org/10.1038/s41467-024-52823-3 | DOI Listing |
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Article Synopsis
- Inherently chiral medium-ring derivatives, crucial for fields like materials science and asymmetric catalysis, face challenges in enantioselective assembly, particularly using organocatalysis.
- Researchers introduce a novel method using N-heterocyclic carbenes (NHC) for a high-order (5 + 3) annulation of specific indolyl compounds with ynals, leading to the efficient creation of diverse eight-membered lactones.
- The study highlights the successful scaling up of production and potential applications of these lactones, demonstrating their practical relevance in synthetic chemistry.