Pure Appl. Chem., 2012, Vol. 84, No. 8, pp. 1673-1684
http://dx.doi.org/10.1351/PAC-CON-11-09-05
Published online 2012-02-03
Accessing chemical diversity by stereoselective gold-catalyzed manipulation of allylic and propargylic alcohols
References
- 1. C. A. , D. R. Fandrick, J. J. Song, C. H. Senanayake. Adv. Synth. Catal. 353, 1825 (2011). (http://dx.doi.org/10.1002/adsc.201100488)
- 2. For selected examples, see.
- 2a. A. S. K. . Angew. Chem., Int. Ed. 44, 6990 (2005). (http://dx.doi.org/10.1002/anie.200502735)
- 2b. A. S. K. . Chem. Rev. 107, 3180 (2007). (http://dx.doi.org/10.1021/cr000436x)
- 2c. A. S. K. . Catal. Today 122, 211 (2007). (http://dx.doi.org/10.1016/j.cattod.2006.10.006)
- 2d. A. , O. D. Davies. Angew. Chem., Int. Ed. 46, 4310 (2007).
- 2e. A. S. K. , M. Rudolph. Chem. Soc. Rev. 37, 1766 (2008). (http://dx.doi.org/10.1039/b615629k)
- 2f. H. C. . Tetrahedron 64, 3885 (2008). (http://dx.doi.org/10.1016/j.tet.2008.01.081)
- 2g. R. , C.-J. Li. Tetrahedron 64, 4917 (2008). (http://dx.doi.org/10.1016/j.tet.2008.03.083)
- 2h. A. . Chem. Rev. 108, 3266 (2008). (http://dx.doi.org/10.1021/cr068435d)
- 2i. D. J. , B. D. Sherry, F. D. Toste. Chem. Rev. 108, 3351 (2008). (http://dx.doi.org/10.1021/cr068430g)
- 2j. N. , N. Krause. Angew. Chem., Int. Ed. 47, 2178 (2008). (http://dx.doi.org/10.1002/anie.200704729)
- 2k. P. , E. Parker. Eur. J. Org. Chem. 6075 (2009). (http://dx.doi.org/10.1002/ejoc.200900790)
- 2l. N. D. , F. D. Toste. Synlett 675 (2010).
- 2m. S. , G. Zhang, L. Zhang. Synlett 692 (2010).
- 3a. M. , M. Tragni. Org. Biomol. Chem. 7, 1501 (2009). (http://dx.doi.org/10.1039/b823217b)
- 3b. N. , N. Kann. Angew. Chem., Int. Ed. 48, 642 (2009). (http://dx.doi.org/10.1002/anie.200804114)
- 3c. E. , R. Sinisi, M. Guiteras Capdevila, D. Petruzziello, F. De Vincentiis, P. G. Cozzi. Eur. J. Org. Chem. 647 (2011). (http://dx.doi.org/10.1002/ejoc.201001474)
- 4a. R. A. . Chem.—Eur. J. 14, 5382 (2008). (http://dx.doi.org/10.1002/chem.200800219)
- 4b. D. J. , B. D. Sherry, F. D. Toste. Chem. Rev. 108, 3351 (2008). (http://dx.doi.org/10.1021/cr068430g)
- 4c. S. , X. Shi. Chem. Cat. Chem. 2, 609 (2010).
- 4d. A. S. K. , C. Hubbert. Angew. Chem., Int. Ed. 49, 1010 (2010). (http://dx.doi.org/10.1002/anie.200906609)
- 4e. A. , P. Y. Toullec, V. Michelet. Synthesis 1501 (2011).
- 5. B. , A. Aponick. Eur. J. Org. Chem. 6605 (2011). (http://dx.doi.org/10.1002/ejoc.201100858)
- 6a. R. J. Sundberg. In The Chemistry of Indoles, Academic Press, New York (1970).
- 6b. R. K. Brown. In Indoles, W. J. Houlihan (Ed.), Wiley-Interscience, New York (1972).
- 6c. R. J. Sundberg. “Pyrroles and their benzoderivatives: Synthesis and applications”, in Comprehensive Heterocyclic Chemistry, Vol. 4, A. R. Katritzky, C. W. Rees (Eds.), p. 313, Pergamon, Oxford (1984).
- 6d. J. A. Joule. “Indole and its derivatives” in Science of Synthesis (Houben-Weyl Methods of Molecular Transformations), Vol. 10, E. J. Thomas (Ed.), Chap. 10.13, Thieme, Stuttgart (2000).
- 7a. M. , A. Eichholzer. Angew. Chem., Int. Ed. 48, 9608 (2009). (http://dx.doi.org/10.1002/anie.200904388)
- 7b. G. , G. Bencivenni, R. Dalpozzo. Chem. Soc. Rev. 39, 4449 (2010). (http://dx.doi.org/10.1039/b923063g)
- 8a. M. , A. Melloni, A. Umani-Ronchi. Angew. Chem., Int. Ed. 43, 550 (2004). (http://dx.doi.org/10.1002/anie.200301679)
- 8b. M. , A. Melloni, S. Tommasi, A. Umani-Ronchi. Synlett 1199 (2005). (http://dx.doi.org/10.1055/s-2005-865210)
- 9. M. , A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi. J. Am. Chem. Soc. 128, 1424 (2006). (http://dx.doi.org/10.1021/ja054109o)
- 10. M. , A. Eichholzer. Angew. Chem., Int. Ed. 48, 9533 (2009). (http://dx.doi.org/10.1002/anie.200904388)
- 11. M. , A. Gualandi, M. Monari, A. Romaniello, D. Savoia, M. Tragni. J. Organomet. Chem. 696, 338 (2011). (http://dx.doi.org/10.1016/j.jorganchem.2010.09.065)
- 12. R. , M. K. S. Vink, H. E. Schoemaker, F. L. van Delft, R. H. Blaauw, F. P. J. T. Rutjes. Synthesis 641 (2004).
- 13a. M. L. , B. R. Rosen, J. P. Wolfe. J. Org. Chem. 74, 5107 (2009) and refs. therein; see also. (http://dx.doi.org/10.1021/jo9007223)
- 13b. H. , Y. Ikeuchi, T. Taguchi, Y. Hanzawa, M. Shiro. J. Am. Chem. Soc. 116, 5469 (1994). (http://dx.doi.org/10.1021/ja00091a061)
- 13c. M. K. , D. Shukla, K. Das. J. Org. Chem. 74, 7013 (2009). (http://dx.doi.org/10.1021/jo901297d)
- 14. M. , A. Eichholzer, A. Gualandi, T. Quinto, D. Savoia. Chem. Cat. Chem. 2, 661 (2010).
- 15. M. , M. Monari, A. Romaniello, M. Tragni. Chem.—Eur. J. 12, 14272 (2010). (http://dx.doi.org/10.1002/chem.201002606)
- 16a. M. , V. Boucard, J.-M. Champagne. J. Am. Chem. Soc. 127, 14180 (2005). (http://dx.doi.org/10.1021/ja0534147)
- 16b. Y. , X. Du, X. Jia, Y. Liu. Adv. Synth. Catal. 351, 1517 (2009). (http://dx.doi.org/10.1002/adsc.200900068)
- 17. Special issue on “Coinage Metals in Organic Synthesis”: Chem. Rev. 8, 2793–3442 (2008).
- 18. I. Ojima (Ed.). Catalytic Asymmetric Synthesis, 3rd ed., Wiley-VCH, Hoboken (2010).
- 19a. A. , C.-Y. Li, B. Biannic. Org. Lett. 10, 669 (2008). (http://dx.doi.org/10.1021/ol703002p)
- 19b. A. , B. Biannic, M. R. Jong. Chem. Commun. 46, 6849 (2010). (http://dx.doi.org/10.1039/c0cc01961e)
- 19c. P. , R. A. Widenhoefer. Org. Lett. 12, 1184 (2010). (http://dx.doi.org/10.1021/ol902923e)
- 19d. A. , B. Biannic. Org. Lett. 13, 1330 (2011). (http://dx.doi.org/10.1039/c1cc11805f)
- 19d. W. P. , K. Stevens, S. G. Lamontb, J. Robertson. Chem. Commun. 47, 7659 (2011).
- 20. B. , T. Ghebreghiorgis, A. Aponick. Beilstein J. Org. Chem. 7, 802 (2011). (http://dx.doi.org/10.3762/bjoc.7.91)
- 21. M. , K. Mikami. Chem.—Eur. J. 17, 13950 (2011). (http://dx.doi.org/10.1002/chem.201103023)
- 22a. A. S. K. . Angew. Chem., Int. Ed. 49, 5232 (2010). (http://dx.doi.org/10.1002/anie.200907078)
- 22b. H. , A. Schier. Chem. Soc. Rev. 41, 370 (2012). (http://dx.doi.org/10.1039/c1cs15182g)
- 23a. C. , A. M. Echavarren. Angew. Chem., Int. Ed. 45, 1105 (2006). (http://dx.doi.org/10.1002/anie.200503484)
- 23b. E. , A. M. Echavarren. Chem. Commun 333 (2007) and refs. therein. (http://dx.doi.org/10.1039/b612008c)
- 23c. S.sF. . Synthesis 3183 (2008). (http://dx.doi.org/10.1055/s-0028-1083164)
- 24a. A. S. K. , M. Rudolph. Chem. Soc. Rev. 37, 1766 (2008). (http://dx.doi.org/10.1039/b615629k)
- 24b. A. . Chem. Soc. Rev. 38, 3208 (2009). (http://dx.doi.org/10.1039/b816696j)
- 25a. C. , C. H. M. Amijs, A. M. Echavarren. Chem.—Eur. J. 13, 1358 (2007). (http://dx.doi.org/10.1002/chem.200601324)
- 25b. C. , A. Escribano-Cuesta, A. M. Echavarren. Tetrahedron 65, 9015 (2009). (http://dx.doi.org/10.1016/j.tet.2009.08.067)
- 26. For a similar Au-catalyzed synthetic approach based on C(2)-alkynyl indoles, see: Y. , W. Xu, X. Wang. Org. Lett. 12, 1448 (2010). (http://dx.doi.org/10.1021/ol100153h)
- 27a. C. , S. Lòpez, A. M. Echavarren. J. Am. Chem. Soc. 127, 6178 (2005). (http://dx.doi.org/10.1021/ja042257t)
- 27b. E. , C. N. Oberhuber, S. Lòpez, J. Benet-Buchholz, A. M. Echavarren. Angew. Chem., Int. Ed. 45, 5455 (2006). (http://dx.doi.org/10.1002/anie.200601688)
- 28. G. , P. Crispino, M. Monari, M. Bandini. Chem. Commun. 47, 7803 (2011). (http://dx.doi.org/10.1039/c1cc12328a)
- 29. The 6-endo-dig mechanism seems not structurally accessible for compounds 6-type, owing to the limited length of the side chain.
- 30. Analogous regiochemical response was reported in literature in the Au-catalyzed hydroindolination of unfunctionalized internal alkynes (see ref. [23]).
