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Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206
Graphical Abstract
Scheme 1: Expectation of the regio- as well as stereoselective reactions of 2.
Scheme 2: Attempts of the present epoxidation to other α,β-unsaturated esters, 1h–j.
Figure 1: Crystallographic structure of the epoxy ring-opening products by PhCH(NH2)Me (3bd) and PhCH2SH (4ba...
Scheme 3: Introduction of additional halogen atoms at the 2-position of the compound 2b.
Scheme 4: Clarification of the stereochemistry of anti,syn-8a and -7b.
Figure 2: Crystallographic structure of anti,syn-8a.
Scheme 5: Reaction of 2b with other stabilized nucleophiles.
Scheme 6: Production of 4,4,4-trifluoro-2,3-dihydroxybutanoate anti-10a.
Scheme 7: Reactions of n-C10H21MgBr-based cuprate with 13f as well as 2b with/without D2O quenching.
Figure 3: A part of 13C NMR spectra for the compounds 11a and 11a-D.