Carbene organic catalytic planar enantioselective macrolactonization

Xiaokang Lv, Fen Su, Hongyan Long, Fengfei Lu, Yukun Zeng, Minghong Liao, Fengrui Che, Xingxing Wu () and Yonggui Robin Chi ()
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Xiaokang Lv: Guizhou University, Huaxi District
Fen Su: Guizhou University, Huaxi District
Hongyan Long: Guizhou University, Huaxi District
Fengfei Lu: Guizhou University, Huaxi District
Yukun Zeng: Guizhou University, Huaxi District
Minghong Liao: Guizhou University, Huaxi District
Fengrui Che: Guizhou University, Huaxi District
Xingxing Wu: Guizhou University, Huaxi District
Yonggui Robin Chi: Guizhou University, Huaxi District

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Macrolactones exhibit distinct conformational and configurational properties and are widely found in natural products, medicines, and agrochemicals. Up to now, the major effort for macrolactonization is directed toward identifying suitable carboxylic acid/alcohol coupling reagents to address the challenges associated with macrocyclization, wherein the stereochemistry of products is usually controlled by the substrate’s inherent chirality. It remains largely unexplored in using catalysts to govern both macrolactone formation and stereochemical control. Here, we disclose a non-enzymatic organocatalytic approach to construct macrolactones bearing chiral planes from achiral substrates. Our strategy utilizes N-heterocyclic carbene (NHC) as a potent acylation catalyst that simultaneously mediates the macrocyclization and controls planar chirality during the catalytic process. Macrolactones varying in ring sizes from sixteen to twenty members are obtained with good-to-excellent yields and enantiomeric ratios. Our study shall open new avenues in accessing macrolactones with various stereogenic elements and ring structures by using readily available small-molecule catalysts.

Date: 2024
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DOI: 10.1038/s41467-024-45218-x

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