Work

Facile enantioselective synthesis of multi-substituted norbornanes/norbornenes using a latent synthon strategy

Year: 2024

Type: article

Abstract: The development of a new catalytic asymmetric synthetic methodology has been following virtually the same pattern in the past decades. Herein, we present a latent synthon strategy within this well-established research domain. By employing substrates containing latent groups, specifically “ON-alkene” in this investigation, a single optimization exercise yields the Diels–Alder adduct with excellent enantiomeric purity. This adduct serves as a universal intermediate, undergoing late-stage diversifications via robust and easily performed synthetic transformations. Consequently, a broad array of structurally diverse chiral norbornanes (NBAs) and norbornenes (NBEs) are obtained with consistent and high enantiomeric purities. Furthermore, our methodology allows for facile asymmetric preparation of chiral NBE ligands as well as the concise synthesis of (+)-gemmacin, ( + )-gemmacin B, and their structural analogs. The development of a new catalytic asymmetric synthetic methodology is of topic of interest. Herein, the authors report a latent synthon strategy, which has been used in the synthesis of a wide range of optically enriched norbornanes with great structural diversity.

Source: Nature Communications

DOI: 10.1038/s41467-024-52644-4

Authors: Zi-An Shen, Jiami Guo, Yixin Lu

Institution: National University of Singapore

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,790

Funders: National University of Singapore, Ministry of Education, India, Faculty of Science, National University of Singapore