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Rationally Designed Chiral Synthons Enabling Asymmetric Z- and E-Selective Vinylogous Aldol Reactions of Aldehydes

Akhil Padarti and Hyunsoo Han*

*Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States, Email: hyunsoo.hanutsa.edu

A. Padarti, H. Han, Org. Lett., 2018, 20, 1448-1452.

DOI: 10.1021/acs.orglett.8b00230 (free Supporting Information)


Abstract

Highly stereoselective 2-oxonia-Cope rearrangement reactions between rationally designed nonracemic vinylogous aldolation synthons and aldehydes provide δ-hydroxy-α,β-unsaturated esters with excellent enantioselectivities and unprecedented Z- and E-selectivities.

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proposed mechanism



Key Words

Cope rearrangement, homoallylic alcohols, 5,6-dihydropyran-2-ones


ID: J54-Y2018