Diastereoselective Synthesis of 1,3-Oxazolidines via Cationic Iron Porphyrin-catalyzed Cycloaddition of Aziridines with Aldehydes

Satoru Teranishi, Kazuki Maeda, Takuya Kurahashi*, Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Email: kurahashi.takuya.2ckyoto-u.ac.jp, matsubara.seijiro.2ekyoto-u.ac.jp

S. Teranishi, K. Maeda, T. Kurahashi, S. Matsubara, Org. Lett., 2019, 21, 2593-2596.

DOI: 10.1021/acs.orglett.9b00560

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Abstract

An efficient iron porphyrin Lewis acid-catalyzed cycloaddition of aziridines with aldehydes provide oxazolidines with high regio- and diastereoselectivity. The cycloaddition proceeds in toluene with 1 mol % of the iron catalyst at 25°C.

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[Fe(TPP)]⁺

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Key Words

1,3-oxazolidines

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ID: J54-Y2019