Organic Letters
Letter
treatment with potassium carbonate in methanol cyclized to
give norbenzomorphan 53 in 86% yield.
REFERENCES
■
(1) Banwell, M. G.; Kelly, B. D.; Kokas, O. J.; Lupton, D. W. Org.
Lett. 2003, 5, 2497.
(2) For some key articles on cross-electrophile couplings, see:
Presumably, these protocols could be readily adapted to the
preparation of the nonracemic forms of these heterocycles
through, for example, enantioselective 1,2-reduction of the
starting enones 7 and 10. In view of the extensive and ongoing
interest in benzomorphans and related systems,18 the processes
outlined in Schemes 4 and 5 should be of considerable utility in
a range of settings.
The possibilities for reductive cyclization of the above-
mentioned cross-coupling products extend beyond those
delineated above, as evidenced by, for example, the report11
that compound 36 (prepared by different means than those
described here) can be engaged in a Cadogan cyclization to give
2-carboethoxy-3-phenylindole in 90% yield. As such, the work
detailed above serves to highlight the capacities of the title
cross-electrophile coupling reactions to deliver a wide range of
products capable of engaging in various useful reductive
cyclization processes, thus forming new or otherwise difficult-
to-access heterocyclic systems.
(a) Knappke, C. E. I.; Grupe, S.; Gartner, D.; Corpet, M.; Gosmini, C.;
̈
Jacobi von Wangelin, A. Chem. - Eur. J. 2014, 20, 6828. (b) Everson, D.
A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793. (c) Hanna, L. E.; Jarvo, E.
R. Angew. Chem., Int. Ed. 2015, 54, 15618. (d) Weix, D. J. Acc. Chem.
Res. 2015, 48, 1767. (e) Poremba, K. E.; Kadunce, N. T.; Suzuki, N.;
Cherney, A. H.; Reisman, S. E. J. Am. Chem. Soc. 2017, 139, 5684.
(3) (a) Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M.
O. Org. Lett. 2004, 6, 2741. (b) Some, S.; Ray, J. K.; Banwell, M. G.;
Jones, M. T. Tetrahedron Lett. 2007, 48, 3609. (c) Banwell, M. G.;
Jones, M. T.; Loong, D. T. J.; Lupton, D. W.; Pinkerton, D. M.; Ray, J.
K.; Willis, A. C. Tetrahedron 2010, 66, 9252. (d) Yan, Q.; Gin, E.;
Wasinska-Kalwa, M.; Banwell, M. G.; Carr, P. D. J. Org. Chem. 2017,
82, 4148. (e) Yan, Q.; Gin, E.; Banwell, M. G.; Willis, A. C.; Carr, P. D.
J. Org. Chem. 2017, 82, 4328.
(4) See: Tang, F.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2016,
81, 10551 and references cited therein.
(5) (a) Herzon, S. B.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 5342.
(b) Nicolaou, K. C.; Nold, A. L.; Li, H. Angew. Chem., Int. Ed. 2009,
48, 5860.
(6) Piers, E.; Grierson, J. R.; Lau, C. K.; Nagakura, I. Can. J. Chem.
1982, 60, 210.
(7) (a) Klement, T.; Rottlander, M.; Tucker, C. E.; Majid, T. N.;
ASSOCIATED CONTENT
■
S
* Supporting Information
̈
The Supporting Information is available free of charge on the
Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201.
(b) Scott, T. L.; Yu, X.; Gorugantula, S. P.; Carrero-Martínez, G.;
Soderberg, B. C. G. Tetrahedron 2006, 62, 10835.
(8) (a) Moss, R. A.; Bracken, K.; Emge, T. J. J. Org. Chem. 1995, 60,
7739. (b) Du, B.; Jiang, X.; Sun, P. J. Org. Chem. 2013, 78, 2786.
̈
Experimental procedures, spectroscopic data, crystallo-
graphic data, and NMR spectra of compounds 5 (X = I,
Br), 7, [1,1′-bis(cyclohexane)]-1,1′-diene-3,3′-dione, 8−
11, 15−19, 24−27, 30−34, 36−47, 49, trans-50, cis-50,
cis-51, 52, 53 and trans-N-(2-(3-chlorocyclopentyl)-
phenyl)-4-methylbenzenesulfonamide (PDF)
(9) Akpinar, G. E.; Kus, M.; Ucuncu, M.; Karakus, E.; Artok, L. Org.
Lett. 2011, 13, 748.
̈
̈
(10) Krizan, T. D.; Martin, J. C. J. Org. Chem. 1982, 47, 2681.
(11) Yamamoto, Y.; Yamada, S.; Nishiyama, H. Adv. Synth. Catal.
2011, 353, 701.
(12) Chunavala, K. C.; Adimurthy, S. Synth. Commun. 2011, 41,
1843.
Accession Codes
(13) Han, J.; Wu, X.; Zhang, Z.; Wang, L. Tetrahedron Lett. 2017, 58,
3433.
(14) Linsenmeier, A. M.; Braje, W. M. Tetrahedron 2015, 71, 6913.
(15) For example, see: Poppe, L.; Tegley, C. M.; Li, V.; Lewis, J.;
Zondlo, J.; Yang, E.; Kurzeja, R. J. M.; Syed, R. J. Am. Chem. Soc. 2009,
131, 16654.
lographic data for this paper. These data can be obtained free of
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033.
(16) Madaan, A.; Verma, R.; Kumar, V.; Singh, A. T.; Jain, S. K.;
Jaggi, M. Arch. Pharm. 2015, 348, 837.
(17) Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata,
M.; Tamaki, K.; Ovaska, T. V.; Smith, C. J.; Wood, J. L. J. Am. Chem.
Soc. 2008, 130, 2087.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
(18) Li, Y.; Feng, C.; Shi, H.; Xu, X. Org. Lett. 2016, 18, 324.
Author Contributions
The manuscript was written through contributions from all of
the authors. All of the authors have given approval to the final
version of the manuscript.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank the Australian Research Council for financial support.
F.K. is the grateful recipient of a scholarship provided by the
Australian National University, and X.L. acknowledges the
support of Circa Pty Ltd (Melbourne), while M.K. thanks the
Higher Education Commission of Pakistan for funding.
D
Org. Lett. XXXX, XXX, XXX−XXX