Key result
Three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions enabled the construction of functionalized chiral β-lactams with high enantioselectivity and efficiency.
Why the study?
Beta-lactam scaffolds are prevalent structural units in antibiotics and natural products, prompting methods to construct alpha-quaternary chiral beta-lactams.
The study presents a practical and sustainable synthetic tool for constructing functionalized chiral β-lactams, which are prevalent structural units in antibiotics and natural products.
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May enable novel chiral β-lactam antibiotics; leaves open clinical validation in resistant infections.
The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved the tandem reaction of alkynes, nitrones and aldehydes (or imines), resulting in the formation of three sequential stereocenters controlled by copper(I) catalysts and chiral bis(oxazolidine) ligands. The developed protocol features high enantioselectivity, good reaction efficiency, and mild operational conditions, representing a practical and sustainable synthetic tool for the construction of functionalized chiral β-lactams.
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Wang et al. (2024) studied this question. Three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions was evaluated on Construction of α-quaternary chiral β-lactams. Three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions enabled the construction of functionalized chiral β-lactams with high enantioselectivity and efficiency.
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