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Catalysis of Cope-type rearrangements of bis-homoallylic hydroxylamines is demonstrated using chiral thiourea derivatives. This formal intramolecular hydroamination reaction provides access to highly enantioenriched ??-substituted pyrrolidine products and represents a complementary approach to metal-catalyzed methods.

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Brown, A. R.; Uyeda, C.; Brotherton, C. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 6747Contributed by Steven Bachrach.Reposted from Computational Organic Chemistry with permissionJacobsen reports on another application of thiourea-based organocatalysts,...
Jacobsen reports on another application of thiourea-based organocatalysts, this time for the catalysis of hydroamination.1 To support the synthetic effort, he examined the uncatalyzed intramolecular hydroamination that takes 1, through TS1 into product 2. The...