Tobias Lauterbach et al.
COMMUNICATIONS
Scheme 3. Proposed mechanism.
and the mixture was stirred at room temperature until the References
reaction was completed. The reaction was quenched with
aqueous saturated NaHCO3 solution, extracted with DCM
and dried over MgSO4. The suspension was filtered and the
solvent was removed under reduced pressure. The crude
product was purified by column chromatography on silica
gel.
[1] For representative reviews on gold catalysis, see: a) G.
Dyker, Angew. Chem. 2000, 112, 4407–4409; Angew.
Chem. Int. Ed. 2000, 39, 4237–4239; b) A. S. K.
Hashmi, Gold Bull. 2003, 36, 3–9; c) A. S. K. Hashmi,
Gold Bull. 2004, 37, 51–65; d) N. Krause, A. Hoff-
mann-Rçder, Org. Biomol. Chem. 2005, 3, 387–391;
e) A. S. K. Hashmi, Angew. Chem. 2005, 117, 7150–
7154; Angew. Chem. Int. Ed. 2005, 44, 6990–6993;
f) A. S. K. Hashmi, G. Hutchings, Angew. Chem. 2006,
118, 8064–8105; Angew. Chem. Int. Ed. 2006, 45, 7896–
7936; g) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395–
403; h) A. Fꢃrstner, P. W. Davies, Angew. Chem. 2007,
119, 3478–3519; Angew. Chem. Int. Ed. 2007, 46, 3410–
3449; i) E. Jimenez-Nunez, A. M. Echavarren, Chem.
Commun. 2007, 333–346; j) A. S. K. Hashmi, Chem.
Rev. 2007, 107, 3180–3211; k) Z. Li, C. Brouwer, C. He,
Chem. Rev. 2008, 108, 3239–3265; l) A. Arcadi, Chem.
Rev. 2008, 108, 3266–3325; m) H. C. Shen, Tetrahedron
2008, 64, 3885–3909; n) H. C. Shen, Tetrahedron 2008,
64, 7847–7870; o) A. S. K. Hashmi, Angew. Chem. 2010,
122, 5360–5369; Angew. Chem. Int. Ed. 2010, 49, 5232–
5241; p) A. Corma, A. Leyva-Pꢄrez, M. J. Sabater,
Chem. Rev. 2011, 111, 1657–1712; q) M. Rudolph,
A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448–2462.
[2] a) J. Xiao, X. Li, Angew. Chem. 2011, 123, 7364–7375;
Angew. Chem. Int. Ed. 2011, 50, 7226–7236; b) M. C.
Blanco, A. S. K. Hashmi, in: Modern Gold Catalyzed
Synthesis, (Eds.: A. S. K. Hashmi, F. D. Toste), Wiley-
VCH, Weinheim, 2012, Chapter 11, pp 273–295.
General Procedure 3 (GP3): Introduction of an
Acetyl Protecting Group
The diyne-ol, 1.10 equiv. DMAP and 1.10 equiv. NEt3 were
dissolved in DCM and 1.10 equiv. acetic anhydride were
added under vigorous stirring. The reaction was monitored
by TLC. After complete conversion of the starting material
the reaction was quenched with a saturated solution of
NaHCO3. The aqueous layer was extracted with DCM and
the combined organic layers were dried with MgSO4, fil-
tered and the solvent was removed under reduced pressure.
The crude product was purified by column chromatography
on silica gel.
General Procedure 4 (GP4): Gold Catalysis
400 mmol diyne were dissolved in 1 mL DCE. 20.0 mmol
(5 mol%) AuCl were added under vigorous stirring and the
mixtrure was heated to 808C. After complete consumption
of the starting material the solvent was removed under re-
duced pressure and the crude product was purified by
column chromatography.
[3] Selected publications, see: a) A. Fꢃrstner, P. Hannen,
Chem. Commun. 2004, 2546–2547; b) M. J. Johansson,
D. J. Gorin, S. T. Staben, F. D. Toste, J. Am. Chem. Soc.
2005, 127, 18002–18003; c) N. Marion, S. P. Nolan,
Angew. Chem. 2007, 119, 2806–2809; Angew. Chem.
Int. Ed. 2007, 46, 2750–2752; d) D. J. Gorin, I. D. G.
Watson, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 3736–
3737; e) A. Correa, N. Marion, L. Fensterbank, M. Mal-
acria, S. P. Nolan, L. Cavallo, Angew. Chem. 2008, 120,
730–733; Angew. Chem. Int. Ed. 2008, 47, 718–721;
Acknowledgements
The authors thank Umicore AG & Co. KG for the generous
donation of gold salts. This work was supported by the DFG
(SFB 623).
6
ꢁ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!