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Chemoselective Switch in the Asymmetric Organocatalysis of 5H-Oxazol-4-ones and N-Itaconimides: Addition-Protonation or [4+2] Cycloaddition

Zhu, Bo; Lee, Richmond; Li, Jiangtao; Ye, Xinyi; Hong, San-Ni; Qiu, Shuai; Coote, Michelle; Jiang, Zhiyong

Description

We report a synthetic strategy for a chemoselective switch and a diastereo-divergent approach for the asymmetric reaction of 5H-oxazol-4-ones and N-itaconimides catalyzed by l-tert-leucine-derived tertiary amine-urea compounds. The reaction was modulated to harness either tandem conjugate addition-protonation or [4+2] cycloaddition as major product with excellent enantio- and diastereoselectivities. Subjecting the enantio-enriched cycloaddition products to a basic silica gel reagent yields the...[Show more]

CollectionsANU Research Publications
Date published: 2016-01-22
Type: Journal article
URI: http://hdl.handle.net/1885/209213
Source: Angewandte Chemie (International ed. in English)
DOI: 10.1002/anie.201507796
Access Rights: Open Access

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