Organic Letters
Letter
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
P.; Dutta, C.; Sarma, B. RSC Adv. 2014, 4, 10912−10917. (i) Dutta,
A. K.; Gogoi, P.; Borah, R. Polyhedron 2017, 123, 184−191.
(
8) Oxidative methods: (a) Deb, M. L.; Dey, S. S.; Bento, I.; Barros,
M. T.; Maycock, C. D. Angew. Chem., Int. Ed. 2013, 52, 9791−9795.
AUTHOR INFORMATION
■
*
(
b) Mahato, S.; Haque, M. A.; Dwari, S.; Jana, C. K. RSC Adv. 2014,
4
, 46214−46217. (c) Deb, M. L.; Pegu, C. D.; Borpatra, P. J.; Baruah,
ORCID
P. K. Tetrahedron Lett. 2016, 57, 5479−5483. (d) Gupta, K. S. V.;
Ramana, D. V.; Vinayak, B.; Sridhar, B.; Chandrasekharam, M. New J.
Chem. 2016, 40, 6389−6395.
(9) Remaining methods: (a) Kumar, G. N.; Subramanian, N. S.;
Author Contributions
Devi, M. R.; Harathi, P.; Sri Latha, N.; Thapaswini, G.; Ravikanth, N.
Int. J. Pharm. Sci. Res. 2014, 5, 3987−3994. (b) Bashier, R. S. M.;
Saeed, A. E. M.; Barakat, E. E. Int. J. Pharm. Sci. Res. 2015, 6, 2103−
2111.
†
P.C. and Y.F.W. contributed equally to this work.
Notes
(
10) (a) Compound 1: Tian, H.; Yu, X.; Li, Q.; Wang, J.; Xu, Q.
The authors declare no competing financial interest.
Adv. Synth. Catal. 2012, 354, 2671−2677. (b) Compound 2: Chen,
M. Z.; McLaughlin, M.; Takahashi, M.; Tarselli, M. A.; Yang, D.;
Umemura, S.; Micalizio, G. C. J. Org. Chem. 2010, 75, 8048−8059.
ACKNOWLEDGMENTS
■
The authors are very appreciative of the support from the
Faculty Senate, the College of Letters and Science, and the
Department of Chemistry and Biochemistry at the University
of California, Santa Barbara. D.Y. was an undergraduate
research participant and recipient of the Lucas Ransom
Scholarship in 2019.
(
c) Compound 3: Mandal, D.; Dolai, R.; Chrysochos, N.; Kalita, P.;
Kumar, R.; Dhara, D.; Maiti, A.; Narayanan, R. S.; Rajaraman, G.;
Schulzke, C.; Chandrasekhar, V.; Jana, A. Org. Lett. 2017, 19, 5605−
5608.
(11) Neuvonen, K.; Pihlaja, K. J. Chem. Soc., Perkin Trans. 2 1988,
4
(
61−467.
12) Compound 7: Anderson, J. C.; Kalogirou, A. S.; Porter, M. J.;
13) Compound 11: Schaufelberger, F.; Timmer, B. J. J.; Ramstrom,
̈
REFERENCES
■
8
(
(
2
1) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311−
352.
O. Chem. Eur. J. 2018, 24, 101−104. Compound 12: Monopoli, A.;
Cotugno, P.; Iannone, F.; Ciminale, F.; Dell’Anna, M. M.; Mastrorilli,
P.; Nacci, A. Eur. J. Org. Chem. 2014, 27, 5925−5931. Compound 13:
Vayer, M.; Morcillo, S. P.; Dupont, J.; Gandon, V.; Bour, C. Angew.
Chem., Int. Ed. 2018, 57, 3228−3232.
(
2) (a) Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51−123.
(
b) Cossio, F. P.; Arrieta, A.; Sierra, M. A. Acc. Chem. Res. 2008, 41,
9
6
7
25−936. (c) Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128,
060−6069. (d) Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 114, 7930−
953. (e) References cited in refs 2a−2d.
(
(
14) Trotter, J. Can. J. Chem. 1959, 37, 1487−1490.
15) Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org.
(
3) (a) Unsworth, W. P.; Kitsiou, C.; Taylor, R. J. K. Org. Lett. 2013,
1
5, 258−261. (b) Unsworth, W. P.; Coulthard, G.; Kitsiou, C.;
Chem. 2001, 66, 4759−4765.
(
(
Taylor, R. J. K. J. Org. Chem. 2014, 79, 1368−1376. (c) References
cited in refs 3a and 3b.
16) Examples 2t−2x in ref 8a.
17) X-ray coordinates and data filed with The Cambridge
(
4) (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am.
Crystallographic Data Centre database (deposition number 1936973).
18) Grell, W.; Hurnaus, R.; Griss, G.; Sauter, R.; Rupprecht, E.;
Mark, M.; Luger, P.; Nar, H.; Wittneben, H.; Muller, P. J. Med. Chem.
998, 41, 5219−5246.
Chem. Soc. 2006, 128, 11040−11041. (b) Martin, S. F. Pure Appl.
(
Chem. 2009, 81, 195−204. (c) Maji, B.; Mayr, H. Z. Z. Naturforsch.,
̈
B: J. Chem. Sci. 2013, 68b, 693−699. (d) Funes-Ardoiz, I.; Gonzalez,
́
1
J.; Santamaría, J.; Sampedro, D. J. Org. Chem. 2016, 81, 1565−1570.
e) Gu, R.; Flidrova, K.; Lehn, J.-M. J. Am. Chem. Soc. 2018, 140,
560−5568.
5) (a) Bohme, T. M.; Augelli-Szafran, C. E.; Hallak, H.; Pugsley, T.;
Serpa, K.; Schwarz, R. D. J. Med. Chem. 2002, 45, 3094−3102.
b) Osyanin, V. A.; Ivleva, E. A.; Osipov, D. V.; Klimochkin, Y. N.
Chem. Heterocycl. Compd. 2011, 47, 845−850. (c) Szatmari, I.; Fulop,
F. Tetrahedron Lett. 2011, 52, 4440−4442. (d) Szatmari, I.;
Heydenreich, M.; Koch, A.; Fulop, F.; Kleinpeter, E. Tetrahedron
013, 69, 7455−7465.
6) (a) Bai, W.-J.; David, J. G.; Feng, Z.-G.; Weaver, M. G.; Wu, K.-
(
5
(
̈
(
́
̈
̈
́
̈
̈
2
(
L.; Pettus, T. R. R. Acc. Chem. Res. 2014, 47, 3655−3664. (b) Feng,
Z.-G.; Bai, W.-J.; Pettus, T. R. R. Angew. Chem., Int. Ed. 2015, 54,
1
864−1867. (c) Feng, Z.-G.; Burnett, G. L.; Pettus, T. R. R. Synlett
018, 29, 1517−1519. (d) Jones, R. M.; Selenski, C.; Pettus, T. R. R.
2
J. Org. Chem. 2002, 67, 6911−6915.
(
7) Thermodynamic methods: (a) Burke, W. J. J. Am. Chem. Soc.
949, 71, 609−612. (b) Burke, W. J.; Stephens, C. W. J. Am. Chem.
Soc. 1952, 74, 1518−1520. (c) Fulop, F.; Lazar, L.; Pelczer, I.;
Bernath, G. Tetrahedron 1988, 44, 2993−2996. (d) Heydenreich, M.;
Koch, A.; Klod, S.; Szatmari, I.; Fulop, F.; Kleinpeter, E. Tetrahedron
006, 62, 11081−11089. (e) Barroso, S.; Abreu, A. M.; Araujo, A. C.;
Coelho, A. M.; Maulide, N.; Martins, A. M. Synlett 2010, 2425−2428.
f) Csutortoki, R.; Szatmari, I.; Koch, A.; Heydenreich, M.;
Kleinpeter, E.; Fulop, F. Tetrahedron 2011, 67, 8564−8571.
g) Shafiee, M.; Khosropour, A. R.; Mohammadpoor-Baltork, I.;
1
̈
̈
́
́
́
́
̈
̈
2
́
(
̈
̈
̈
́
̈
̈
(
Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Khavasi, H. R.
Mol. Diversity 2012, 16, 727−735. (h) Borah, R.; Dutta, A. K.; Sarma,
D
Org. Lett. XXXX, XXX, XXX−XXX