Titanium(IV) catalyzed cycloadditions of N-sulfonyl nitrones

ORGN 294

Katherine M. Partridge, partridge@wisc.edu, Department of Chemistry, University of Wisconsin - Madison, 1101 University Ave, Madison, WI 53706 and Tehshik P. Yoon, tyoon@chem.wisc.edu, Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI 53706.
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 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.

 

Heterocycles and Aromatics
8:00 AM-11:40 AM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008