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Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

Farzaneh Soleymani Movahed, Siong Wan Foo, Shogo Mori, Saeko Ogawa and Susumu Saito*

*Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan, Email: saito.susumuf.mbox.nagoya-u.ac.jp

F. S. Movahed, S. W. Foo, S. Mori, S. Ogawa, S. Saito, J. Org. Chem., 2022, 87, 243-257.

DOI: 10.1021/acs.joc.1c02318


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Abstract

Low loadings of a 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst promote a metal-free, biomimetic cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines in very good yields. This dehydrative cyclization exhibits a broad substrate scope and high functional-group tolerance can can be conducted on a gram scale.


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proposed mechanism



Key Words

2-oxazolines, organocatalysis


ID: J42-Y2022