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(21) Typical Procedure (Compound 4a): To a degassed
solution of [PdCl2(PPh3)2] (4.4 mg, 0.0064 mmol) in
anhydrous THF (2 mL) in a Schlenk tube, allyltributyl-
stannane 3 (85.2 mg, 0.25 mmol) was added followed by
allyl chloride 2 (19.6 mg, 0.25 mmol). To this, 1a (42.02 mg,
0.12 mmol) was added (in THF) and the mixture was stirred
at room temperature for 8 h. After the completion of the
reaction (as evident by TLC), the solvent was removed under
reduced pressure and the residue was purified by using silica
gel (100–200 mesh) column chromatography (EtOAc–
hexane, 12%) to afford 4a (41.1 mg, 78%).
(22) Spectral Data of 4a: Rf = 0.46 (EtOAc–hexane, 4:6); IR
(neat): 3079, 2955, 2919, 2850, 2313, 2246, 1734, 1604,
1510, 1461, 1376, 1290, 1248, 1177, 1118, 1032 cm–1; 1H
NMR (500 MHz, CDCl3): δ = 7.26–7.24 (m, 1 H), 7.08 (d,
J = 8.5 Hz, 1 H), 6.98–6.94 (m, 2 H), 5.94–5.86 (m, 1 H),
5.56–5.47 (m, 1 H), 5.42–5.35 (m, 2 H), 5.05–4.98 (m, 2 H),
3.89 (s, 3 H), 3.84 (s, 3 H), 3.72 (s, 3 H), 3.18–3.15 (m, 1 H),
2.87–2.75 (m, 2 H), 2.63–2.58 (m, 1 H), 2.27–2.21 (m, 1 H);
13C NMR (125 MHz, CDCl3): δ = 171.0, 166.0, 160.4,
137.4, 136.6, 134.0, 131.1, 130.1, 128.7, 126.0, 123.5,
118.1, 114.5, 114.3, 113.7 (2C), 55.3, 52.6, 52.5, 48.2, 42.7,
42.5, 33.8; HRMS (ESI): m/z [M + Na]+ calcd for
C23H24N2NaO5: 431.15829; found: 431.15646.
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Tetrahedron Lett. 2012, 53, 1210. (b) Nakamura, H.;
(23) CCDC-933875.
Synlett 2014, 25, 359–364
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