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LETTER
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Allyl Esters; General Procedure: A suspension of
PdEnCat 30 (Aldrich; 0.4 mmol/g loading, 0.05 equiv) in
THF–H2O (9:1, 5 mL) was bubbled with argon for 10 min.
After this time, DCHT (0.15 equiv) and the corresponding
allyl ester 1 (1.0 equiv, 70 mg) were added under positive
pressure. Finally, PhSiH3 was injected (2.0 equiv), and the
mixture was allowed to react for 2 h at r.t. under an argon
atmosphere. After this time, the reaction was filtered through
Celite and the filtrate was evaporated under reduced
pressure. The remaining solid was dissolved with EtOAc (20
mL) and washed with H2O (3 × 10 mL) and brine (3 × 10
mL). The organic layer was dried (MgSO4) and evaporated
under vacuum. Purification by solid-phase extraction (C18
reverse-phase chromatography, H2O/MeOH) gave pure
carboxylic acids 2 (yields shown in Table 1). Purity was
determined by HPLC, 1H NMR and 13C NMR analyses. All
the carboxylic acids are commercially available. The
recorded 1H and 13C NMR spectra of the synthesized
compounds were consistent with those registered for
commercial samples.
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Synlett 2014, 25, 2319–2322
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