3 years ago

Highly Stereoselective 2-Oxonia-Cope Rearrangement: A Platform Enabling At-Will Control of Regio-, Enantio-, and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes

Highly Stereoselective 2-Oxonia-Cope Rearrangement:
A Platform Enabling At-Will Control of Regio-, Enantio-,
and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes
Hyunsoo Han, Dongeun Kim, Akhil Padarti
A distinctly different approach for the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without the regioselectivity issue associated with traditional vinylogous aldol reactions.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03895

DOI: 10.1021/acs.orglett.7b03895

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