Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 10, Pages 2920-2921Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja711335d
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- NCRR NIH HHS [RR08389-01] Funding Source: Medline
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We have developed cycloaddition reactions of novel, electron-deficient N-nosyl nitrones that arise from the titanium(IV)-catalyzed rearrangement of the corresponding N-nosyl oxaziridines. A diverse range of styrenes and oxaziridines react smoothly in this transformation, producing structurally varied N-nosyl isoxazolidines in good yields and with excellent diastereoselectivity. Importantly, the nosyl protecting group can be easily removed under mild conditions without concomitant cleavage of the sensitive isoxazolidine nitrogen-oxygen bond, allowing efficient access to N-unsubstituted isoxazolidines for further synthetic manipulation and biological evaluation.
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