Substrate Directed Regio‐ and Enantioselective Ring‐Opening of Epoxides and Aziridines

The oxirane and aziridine rings are valuable building blocks in modern synthetic chemistry and catalytic asymmetric ring opening reactions of these three membered ring systems have emerged as a powerful chemical tool for the synthesis of natural products and biologically active compounds. In this co...

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Bibliographic Details
Published in:ChemCatChem 2024-04, Vol.16 (8), p.n/a
Main Authors: Sun, Wen‐Na, Mei, Guang‐Jian, Jia, Shi‐Kun
Format: Article
Language:English
Subjects:
Alcohols
aziridine
Catalysis
Chemical synthesis
directing group
Enantiomers
epoxide
Ethylene oxide
kinetic resolution
Natural products
Ring opening
ring-opening reaction
Substrates
Zinc compounds
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Summary:The oxirane and aziridine rings are valuable building blocks in modern synthetic chemistry and catalytic asymmetric ring opening reactions of these three membered ring systems have emerged as a powerful chemical tool for the synthesis of natural products and biologically active compounds. In this context, the regioselective ring‐opening of structurally or electronically unbiased epoxides and aziridines is challenging. Recently, metal‐catalyzed substrate directed strategies have successfully applied in the regio‐ and enantioselective ring opening of functionalized epoxy alcohols by the Yamamoto group. Subsequently, our group realized the ring opening reactions of functionalized 2,3‐aziridinyl alcohols with the dinuclear zinc complex. These enantioselective nucleophilic ring opening reactions of functionalized epoxy alcohols and aziridinyl alcohols allow for the facile synthesis of amino alcohol derivatives and the introduction of new concepts in catalysis. In this concept article, we try to give a timely summary of substrate directed regio‐ and enantioselective ring opening of epoxides and aziridines. Substrates including 2,3‐epoxy alcohols, 3,4‐epoxy alcohols, 2,3‐epoxy sulfonamides, 3,4‐epoxy amides, 3,4‐epoxy esters, 2‐acyl‐3‐aryl‐N‐tosylaziridines, and 2,3‐aziridinyl alcohols were successfully adopted in enantioselective ring openings with various nucleophiles, making a wide range of amino alcohol derivatives chemically available.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.202301431