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Experimental Section
General Procedure for the Hydrocyanative
Cyclization; Synthesis of 15a
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A
solution of 14a (0.12 mmol), P(OPh)3 (15.9 mL,
0.06 mmol), Ni[P(OPh)3]4 (0.012 mmol, 15.8 mg) and ace-
tone cyanohydrin (0.22 mL, 2.42 mmol) in toluene (0.12 mL)
was heated at 1008C for 1 h under an argon atmosphere.
The reaction mixture was poured onto silica gel to be puri-
fied by column chromatography (n-hexane/AcOEt=15/1) to
give 15a as colorless solid; yield: 29.7 mg (72%); mp 97–
1
1008C. H NMR (CDCl3, 400 MHz): d=0.71–0.77 (m, 2H),
0.83–0.89 (m, 2H), 1.23–1.30 (m, 1H), 1.45 (s, 3H), 2.46 (s,
3H), 3.08 (d, 1H, J=9.6 Hz), 3.15 (d, 1H, J=9.6 Hz), 3.95
(d, 1H, J=16.0 Hz), 4.09 (d, 1H, J=16.0 Hz), 5.19 (d, 1H,
J=17.2 Hz), 5.21 (d, 1H, J=10.4 Hz), 5.78 (dd, 1H, J=17.2,
10.4 Hz), 7.37 (d, 2H, J=8.0 Hz), 7.71 (d, 2H, J=8.0 Hz);
13C NMR (CDCl3, 100 MHz): d=6.3, 6.4, 7.8, 12.2, 21.6,
49.1, 52.2, 60.4, 110.4, 113.9, 115.8, 128.0, 129.9, 131.5, 138.4,
144.3, 157.9; IR (ATR) n: 2929, 2215, 1597, 1486, 1347,
1161 cmÀ1
;
HR-MS (ESI): m/z=365.1317, calcd. for
C19H22N2NaO2S [M+Na]+: 365.1300.
[8] For a multi-component coupling reaction, see: a) T. Ig-
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Acknowledgements
The authors are grateful for financial support from KAKEN-
HI (21590003 for S.A. and 15J04214 for H.H.), the Uehara
Memorial Foundation (S.A.) and The Naito Foundation
(S.A.).
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