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Fig. 1 Proposed transition state.
application of this new methodology in total synthesis are
currently ongoing in our laboratory.
We thank the Spanish Ministry of Science and Innovation
(MICINN) for financial support (Project AYA2009-13920-
C02-02). A.-N. R. Alba and X. Companyo are also grateful
to MICINN and to the Generalitat de Catalunya, respectively,
for their pre-doctoral fellowships.
Notes and references
z Experimental Section
To a flask containing a solution of the oxazol-5-one (0.078 mmol,
1.5 equiv.) and the corresponding catalyst (0.0052 mmol, 0.1 equiv.) at
the desired temperature in toluene (0.5 mL), 1,2-bis(phenylsulfonyl)-
ethylene (16 mg, 0.052 mmol, 1 equiv.) was added in one portion. The
reaction mixture was stirred at this temperature after completion. The
crude was purified by column chromatography to afford compound 3.
3a: Colorless oil. 1H NMR (300 MHz, CDCl3): d = 8.08–8.05
(m, 2H), 8.01–7.98 (m, 2H), 7.83–7.81 (m, 2H), 7.64–7.51 (m, 6H),
7.44–7.39 (m, 2H), 5.05 (dd, J = 8.2 Hz, J = 2.6 Hz, 1H), 2.89 (dd,
J = 16.4 Hz, J = 2.3 Hz, 1H), 2.74 (dd, J = 16.1 Hz, J = 7.9 Hz, 1H),
2.08 (h, J = 6.7 Hz, 1H), 0.98 (d J = 6.7 Hz, 1H), 0.95 (d, J = 6.7 Hz,
1H); 13C NMR (75 MHz, CDCl3): d = 206.9, 162.0, 137.3, 136.9,
134.7, 134.6, 133.1, 130.0, 129.7, 129.1, 128.8, 128.2, 79.3, 72.3, 37.4,
30.9, 29.5, 16.4,; HRMS (ESI): calcd. for [M+H]+ (C26H26NO6S2)
requires 512.1196, found 512.1198. HPLC (Chiralpak IA, n-hexane :
i-PrOH = 80 : 20, l = 254 nm, 1.0 mL minꢁ1): tR = 9.5, 12.4 min.
[a]2D5 = ꢁ11.2 (c = 0.77, CHCl3, 95% ee).
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ꢀc
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