H.-J. Yang, F.-J. Xiong, X.-F. Chen, F.-E. Chen
SHORT COMMUNICATION
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Experimental Section
Typical Procedure for the Enantioselective Thiolysis of Prochiral
Cyclic Anhydrides with Catalyst 5a: Phenylmethanethiol (30 μL,
0.24 mmol) was added to
a stirred solution of 5a (30 mg,
0.04 mmol) and 7 (31 mg, 0.20 mmol) in MTBE (2.0 mL) at –20 °C
under nitrogen. When TLC analysis indicated complete consump-
tion of the anhydride, TMSCH2N2 (0.40 mmol) and methanol
(200 μL) were consecutively added. The solution was stirred at
room temperature for 30 min and then concentrated under vacuum
to give a crude product. Purification of the crude product by col-
umn chromatography (silica gel; petroleum ether/EtOAc, 8:1) fur-
nished thioester 8 (52 mg, 93%). HPLC (Chiralcel OD-H, hexane/
iPrOH = 80:20, flow rate = 0.50 mLmin–1, T = 30 °C, λ = 254 nm):
tR = 11.2 (major), 10.2 min (minor). [α]2D5 = –3.3 (c = 0.7, CHCl3).
1H NMR (400 MHz, CDCl3): δ = 1.04 (d, J = 6.4 Hz, 3 H), 2.26
(dd, J = 15.2, 7.2 Hz, 1 H), 2.41 (dd, J = 15.2, 5.2 Hz, 1 H), 2.49–
2.69 (m, 3 H), 3.68 (s, 3 H), 7.25–7.33 ppm (m, 5 H). 13C NMR
(100 MHz, CDCl3): δ = 19.97, 28.44, 33.57, 40.82, 50.15, 51.83,
127.56, 128.93, 129.10, 137.87, 172.88, 197.78 ppm.
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Received: March 31, 2013
Published Online: June 17, 2013
4498
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Eur. J. Org. Chem. 2013, 4495–4498