The combined use of asymmetric Au(I) catalysis with allylic as well as propargylic alcohols proved to be a competent synthetic tool, toward the realization of complex molecular organic architectures in a stereochemically defined manner. In particular, allylic alcohols have been utilized as alkylating agents in the synthesis of tetrahydrocarbazoles/carbolines and morpholines by means of new C–C and C–X bond-forming processes. Analogously, the direct activation of indole-propargylic alcohols with cationic Au complexes opened a direct access to tetracyclic fused indolines in a highly stereoselective manner.
Conference
International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 16th, Shanghai, China, 2011-07-24–2011-07-28
References
1 10.1002/adsc.201100488, C. A. Busacca, D. R. Fandrick, J. J. Song, C. H. Senanayake. Adv. Synth. Catal.353, 1825 (2011).Search in Google Scholar
2 For selected examples, see.Search in Google Scholar
2a 10.1002/anie.200502735, A. S. K. Hashmi. Angew. Chem., Int. Ed.44, 6990 (2005).Search in Google Scholar PubMed
2b 10.1021/cr000436x, A. S. K. Hashmi. Chem. Rev.107, 3180 (2007).Search in Google Scholar PubMed
2c 10.1016/j.cattod.2006.10.006, A. S. K. Hashmi. Catal. Today122, 211 (2007).Search in Google Scholar
2d A. Fürstner, O. D. Davies. Angew. Chem., Int. Ed.46, 4310 (2007).Search in Google Scholar
2e 10.1039/b615629k, A. S. K. Hashmi, M. Rudolph. Chem. Soc. Rev.37, 1766 (2008).Search in Google Scholar PubMed
2f 10.1016/j.tet.2008.01.081, H. C. Shen. Tetrahedron64, 3885 (2008).Search in Google Scholar
2g 10.1016/j.tet.2008.03.083, R. Skouta, C.-J. Li. Tetrahedron64, 4917 (2008).Search in Google Scholar
2h 10.1021/cr068435d, A. Arcadi. Chem. Rev.108, 3266 (2008).Search in Google Scholar PubMed
2i 10.1021/cr068430g, D. J. Gorin, B. D. Sherry, F. D. Toste. Chem. Rev.108, 3351 (2008).Search in Google Scholar PubMed PubMed Central
2j 10.1002/anie.200704729, N. Bongers, N. Krause. Angew. Chem., Int. Ed.47, 2178 (2008).Search in Google Scholar PubMed
2k 10.1002/ejoc.200900790, P. Belmont, E. Parker. Eur. J. Org. Chem. 6075 (2009).Search in Google Scholar
2l N. D. Shapiro, F. D. Toste. Synlett 675 (2010).10.1055/s-0029-1219369Search in Google Scholar PubMed PubMed Central
2m S. Wang, G. Zhang, L. Zhang. Synlett 692 (2010).10.1055/s-0029-1219527Search in Google Scholar
3a 10.1039/b823217b, M. Bandini, M. Tragni. Org. Biomol. Chem.7, 1501 (2009).Search in Google Scholar PubMed
3b 10.1002/anie.200804114, N. Ljungdahl, N. Kann. Angew. Chem., Int. Ed.48, 642 (2009).Search in Google Scholar PubMed
3c 10.1002/ejoc.201001474, E. Emer, R. Sinisi, M. Guiteras Capdevila, D. Petruzziello, F. De Vincentiis, P. G. Cozzi. Eur. J. Org. Chem. 647 (2011).Search in Google Scholar
4a 10.1002/chem.200800219, R. A. Widenhoefer. Chem.—Eur. J.14, 5382 (2008).Search in Google Scholar PubMed
4b 10.1021/cr068430g, D. J. Gorin, B. D. Sherry, F. D. Toste. Chem. Rev.108, 3351 (2008).Search in Google Scholar PubMed PubMed Central
4c S. Sengupta, X. Shi. Chem. Cat. Chem.2, 609 (2010).Search in Google Scholar
4d 10.1002/anie.200906609, A. S. K. Hashmi, C. Hubbert. Angew. Chem., Int. Ed.49, 1010 (2010).Search in Google Scholar PubMed
4e A. Pradal, P. Y. Toullec, V. Michelet. Synthesis 1501 (2011).10.1055/s-0030-1258465Search in Google Scholar
5 10.1002/ejoc.201100858, B. Biannic, A. Aponick. Eur. J. Org. Chem. 6605 (2011).Search in Google Scholar
6a R. J. Sundberg. In The Chemistry of Indoles, Academic Press, New York (1970).Search in Google Scholar
6b R. K. Brown. In Indoles, W. J. Houlihan (Ed.), Wiley-Interscience, New York (1972).Search in Google Scholar
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).Search in Google Scholar
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).Search in Google Scholar
7a 10.1002/anie.200904388, M. Bandini, A. Eichholzer. Angew. Chem., Int. Ed.48, 9608 (2009).Search in Google Scholar PubMed
7b 10.1039/b923063g, G. Bartoli, G. Bencivenni, R. Dalpozzo. Chem. Soc. Rev.39, 4449 (2010).Search in Google Scholar PubMed
8a 10.1002/anie.200301679, M. Bandini, A. Melloni, A. Umani-Ronchi. Angew. Chem., Int. Ed.43, 550 (2004).Search in Google Scholar PubMed
8b 10.1055/s-2005-865210, M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi. Synlett 1199 (2005).Search in Google Scholar
9 10.1021/ja054109o, M. Bandini, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi. J. Am. Chem. Soc.128, 1424 (2006).Search in Google Scholar PubMed
10 10.1002/anie.200904388, M. Bandini, A. Eichholzer. Angew. Chem., Int. Ed.48, 9533 (2009).Search in Google Scholar
11 10.1016/j.jorganchem.2010.09.065, M. Bandini, A. Gualandi, M. Monari, A. Romaniello, D. Savoia, M. Tragni. J. Organomet. Chem.696, 338 (2011).Search in Google Scholar
12 R. Wijtmans, M. K. S. Vink, H. E. Schoemaker, F. L. van Delft, R. H. Blaauw, F. P. J. T. Rutjes. Synthesis 641 (2004).10.1055/s-2004-816003Search in Google Scholar
13a 10.1021/jo9007223, M. L. Leathen, B. R. Rosen, J. P. Wolfe. J. Org. Chem.74, 5107 (2009) and refs. therein; see also.Search in Google Scholar PubMed PubMed Central
13b 10.1021/ja00091a061, H. Ito, Y. Ikeuchi, T. Taguchi, Y. Hanzawa, M. Shiro. J. Am. Chem. Soc.116, 5469 (1994).Search in Google Scholar
13c 10.1021/jo901297d, M. K. Ghorai, D. Shukla, K. Das. J. Org. Chem.74, 7013 (2009).Search in Google Scholar PubMed
14 M. Bandini, A. Eichholzer, A. Gualandi, T. Quinto, D. Savoia. Chem. Cat. Chem.2, 661 (2010).Search in Google Scholar
15 10.1002/chem.201002606, M. Bandini, M. Monari, A. Romaniello, M. Tragni. Chem.—Eur. J.12, 14272 (2010).Search in Google Scholar PubMed
16a 10.1021/ja0534147, M. Georgy, V. Boucard, J.-M. Champagne. J. Am. Chem. Soc.127, 14180 (2005).Search in Google Scholar PubMed
16b 10.1002/adsc.200900068, Y. Lu, X. Du, X. Jia, Y. Liu. Adv. Synth. Catal.351, 1517 (2009).Search in Google Scholar
17 Special issue on “Coinage Metals in Organic Synthesis”: Chem. Rev.8, 2793–3442 (2008).10.1021/cr800415xSearch in Google Scholar PubMed
18 I. Ojima (Ed.). Catalytic Asymmetric Synthesis, 3rd ed., Wiley-VCH, Hoboken (2010).10.1002/9780470584248Search in Google Scholar
19a 10.1021/ol703002p, A. Aponick, C.-Y. Li, B. Biannic. Org. Lett.10, 669 (2008).Search in Google Scholar PubMed
19b 10.1039/c0cc01961e, A. Aponick, B. Biannic, M. R. Jong. Chem. Commun.46, 6849 (2010).Search in Google Scholar PubMed
19c 10.1021/ol902923e, P. Mukherjee, R. A. Widenhoefer. Org. Lett.12, 1184 (2010).Search in Google Scholar PubMed PubMed Central
19d 10.1039/c1cc11805f, A. Aponick, B. Biannic. Org. Lett.13, 1330 (2011).Search in Google Scholar PubMed
19d W. P. Unsworth, K. Stevens, S. G. Lamontb, J. Robertson. Chem. Commun.47, 7659 (2011).Search in Google Scholar
20 10.3762/bjoc.7.91, B. Biannic, T. Ghebreghiorgis, A. Aponick. Beilstein J. Org. Chem.7, 802 (2011).Search in Google Scholar PubMed PubMed Central
21 10.1002/chem.201103023, M. Kojima, K. Mikami. Chem.—Eur. J.17, 13950 (2011).Search in Google Scholar PubMed
22a 10.1002/anie.200907078, A. S. K. Hashmi. Angew. Chem., Int. Ed.49, 5232 (2010).Search in Google Scholar PubMed
22b 10.1039/c1cs15182g, H. Schmidbaur, A. Schier. Chem. Soc. Rev.41, 370 (2012).Search in Google Scholar PubMed
23a 10.1002/anie.200503484, C. Ferrer, A. M. Echavarren. Angew. Chem., Int. Ed.45, 1105 (2006).Search in Google Scholar PubMed
23b 10.1039/b612008c, E. Jiménez-Núñez, A. M. Echavarren. Chem. Commun 333 (2007) and refs. therein.Search in Google Scholar PubMed
23c 10.1055/s-0028-1083164, S.sF. Kirsch. Synthesis 3183 (2008).Search in Google Scholar
24a 10.1039/b615629k, A. S. K. Hashmi, M. Rudolph. Chem. Soc. Rev.37, 1766 (2008).Search in Google Scholar PubMed
24b 10.1039/b816696j, A. Fürstner. Chem. Soc. Rev.38, 3208 (2009).Search in Google Scholar PubMed
25a 10.1002/chem.200601324, C. Ferrer, C. H. M. Amijs, A. M. Echavarren. Chem.—Eur. J.13, 1358 (2007).Search in Google Scholar PubMed
25b 10.1016/j.tet.2009.08.067, C. Ferrer, A. Escribano-Cuesta, A. M. Echavarren. Tetrahedron65, 9015 (2009).Search in Google Scholar
26 10.1021/ol100153h, For a similar Au-catalyzed synthetic approach based on C(2)-alkynyl indoles, see: Y. Liu, W. Xu, X. Wang. Org. Lett.12, 1448 (2010).Search in Google Scholar PubMed
27a 10.1021/ja042257t, C. Nieto-Oberhuber, S. Lòpez, A. M. Echavarren. J. Am. Chem. Soc.127, 6178 (2005).Search in Google Scholar PubMed
27b 10.1002/anie.200601688, E. Herrero-Gómez, C. N. Oberhuber, S. Lòpez, J. Benet-Buchholz, A. M. Echavarren. Angew. Chem., Int. Ed.45, 5455 (2006).Search in Google Scholar PubMed
28 10.1039/c1cc12328a, G. Cera, P. Crispino, M. Monari, M. Bandini. Chem. Commun.47, 7803 (2011).Search in Google Scholar PubMed
29 The 6-endo-dig mechanism seems not structurally accessible for compounds 6-type, owing to the limited length of the side chain.Search in Google Scholar
30 Analogous regiochemical response was reported in literature in the Au-catalyzed hydroindolination of unfunctionalized internal alkynes (see ref. [23]).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston