Paper
RSC Advances
sequence provides an interesting entry to aliphatic primary 15 G.-J. ten Brink, I. W. C. E. Arends and R. A. Sheldon, Adv.
amines merely isolated aer simple acid–base extraction. Synth. Catal., 2002, 344, 355–369.
Finally, the generated phorone 3 could readily be recycled into 16 A. Vasseur, R. Membrat, D. Gatineau, A. Tenaglia, D. Nuel
2,2,6,6-tetramethylpiperidin-4-ol by reacting with ammonia and and L. Giordano, ChemCatChem, 2017, 9, 728–732.
the method is practicable on a large scale (see ESI†). The 17 P. M. Castro, H. Gulyas, J. Benet-Buchholz, C. Bo, Z. Freixa
´
proposed mechanism for this sequence clearly shows the mul-
tiskilling aspect of M/PAP catalysts.
and P. W. N. M. van Leeuwen, Catal. Sci. Technol., 2011, 1,
401.
18 R. Membrat, A. Vasseur, A. Martinez, L. Giordano and
D. Nuel, Eur. J. Org. Chem., 2018, 2018, 5427–5434.
19 J. Bigeault, I. de Riggi, Y. Gimbert, L. Giordano and
G. Buono, Synlett, 2008, 2008, 1071–1075.
20 T. Achard, CHIMIA International Journal for Chemistry, 2016,
70, 8–19.
Conflicts of interest
There are no conicts to declare.
Acknowledgements
´
21 J.-Y. Laronze, J. Sapi and J. Levy, Synthesis, 1988, 1988, 619–
`
This work was supported by Ministere de l'Enseignement
621.
´
Superieur et de la Recherche (R. Membrat PhD grant). The
´
22 J. Levy, J.-Y. Laronze and J. Sapi, Tetrahedron Lett., 1988, 29,
´
authors want to thank Dr. Valerie Monnier and Dr Christophe
3303–3306.
Chendo for ESI-MS experiments and Dr Alphonse Tenaglia for
fruitful discussions. Umicore AG & Co. KG is acknowledged for
the generous gi of platinum complexes.
23 P. Aschwanden, C. R. J. Stephenson and E. M. Carreira, Org.
Lett., 2006, 8, 2437–2440.
24 M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445–
7455.
25 H. Shi, D. J. Babinski and T. Ritter, J. Am. Chem. Soc., 2015,
137, 3775–3778.
26 H. Seo, M. H. Katcher and T. F. Jamison, Nat. Chem., 2017, 9,
453–456.
Notes and references
1 J. Muzart, Eur. J. Org. Chem., 2015, 2015, 5693–5707.
2 D. Wang and D. Astruc, Chem. Rev., 2015, 115, 6621–6686.
3 B. Karimi and A. Zamani, J. Iran. Chem. Soc., 2008, 5, S1–S20.
4 D. Wang, A. B. Weinstein, P. B. White and S. S. Stahl, Chem.
Rev., 2018, 118, 2636–2679.
5 J. Muzart, Tetrahedron, 2003, 59, 5789–5816.
6 B. Ding, Z. Zhang, Y. Liu, M. Sugiya, T. Imamoto and
W. Zhang, Org. Lett., 2013, 15, 3690–3693.
7 Y. Tsuchiya, Y. Hamashima and M. Sodeoka, Org. Lett., 2006,
8, 4851–4854.
8 K. M. Gligorich, S. A. Cummings and M. S. Sigman, J. Am.
Chem. Soc., 2007, 129, 14193–14195.
9 S. M. Podhajsky, Y. Iwai, A. Cook-Sneathen and M. S. Sigman,
Tetrahedron, 2011, 67, 4435–4441.
10 H. Hikawa, T. Koike, K. Izumi, S. Kikkawa and I. Azumaya,
Adv. Synth. Catal., 2016, 358, 784–791.
11 S. M. Podhajsky and M. S. Sigman, Organometallics, 2007, 26,
5680–5686.
12 M. J. Spallek, S. Stockinger, R. Goddard and O. Trapp, Adv.
Synth. Catal., 2012, 354, 1466–1480.
27 1,4 Addition products and polymers were detected by 1H
NMR spectroscopy and low resolution ESIMS experiments.
28 R. Membrat, A. Vasseur, L. Giordano, A. Martinez and
D. Nuel, Tetrahedron Lett., 2019, 60, 240–243.
29 For aliphatic electrophiles, see the procedure in the ESI
(Section 2.3†).
30 For procedure and yield see ESI (Section 2.5†).
31 The fact that 1s is less reactive than the other 1 substrates
clearly stress that the presence of the two methyl groups in
a position due to the nitrogen atom is crucial for the ring
opening to occur (see ref. 34).
32 T. Ravindran, R. Jeyaraman, R. W. Murray and M. Singh, J.
Org. Chem., 1991, 56, 4833–4840.
33 A. M. Belostotskii and A. B. Shapiro, Chem. Heterocycl.
Compd., 1984, 20, 761–766.
34 A. M. Belostotskii and A. B. Shapiro, Chem. Heterocycl.
Compd., 1987, 23, 665–669.
35 S. Kobayashi, T. Busujima and S. Nagayama, Chem.–Eur. J.,
2000, 6, 3491–3494.
13 O. Kose and S. Saito, Org. Biomol. Chem., 2010, 8, 896–900.
´
´
14 A. Martınez-Asencio, M. Yus and D. J. Ramon, Synthesis,
2011, 2011, 3730–3740.
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