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.han
utsa.edu
A. Padarti, H. Han, Org. Lett., 2018, 20, 1448-1452.
DOI: 10.1021/acs.orglett.8b00230
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.
see article for more examples
proposed mechanism
Key Words
Cope rearrangement, homoallylic alcohols, 5,6-dihydropyran-2-ones
ID: J54-Y2018
