Organic & Biomolecular Chemistry
Paper
cyclic scaffolds (morpholines, aziridines, and piperazines) 20 D. Riber, R. Hazell and T. Skrydstrup, J. Org. Chem., 2000,
starting from the synthesized β-tert-amino alcohols.
65, 5382–5390.
21 L. J. Rono, H. G. Yayla, D. Y. Wang, M. F. Armstrong and
R. R. Knowles, J. Am. Chem. Soc., 2013, 135, 17735–17738.
22 H. Huo, X. Shen, C. Wang, L. Zhang, P. Röse, L.-A. Chen,
K. Harms, M. Marsch, G. Hilt and E. Meggers, Nature,
2014, 515, 100–103.
Conflicts of interest
There are no conflicts to declare.
23 J. Ma, K. Harms and E. Meggers, Chem. Commun., 2016, 52,
10183–10186.
Acknowledgements
24 C. Wang, J. Qin, X. Shen, R. Riedel, K. Harms and
E. Meggers, Angew. Chem., Int. Ed., 2016, 55, 685–688.
25 C.-X. Ye, Y. Y. Melcamu, H.-H. Li, J.-T. Cheng, T.-T. Zhang,
Y.-P. Ruan, X. Zheng, X. Lu and P.-Q. Huang, Nat.
Commun., 2018, 9, 410.
26 J. L. Schwarz, R. Kleinmans, T. O. Paulisch and F. Glorius,
J. Am. Chem. Soc., 2020, 142, 2168–2174.
27 R. Wang, M. Ma, X. Gong, X. Fan and P. J. Walsh, Org. Lett.,
2019, 21, 27–31.
The authors are grateful to the National Science Centre of
Poland for financial support of the project (research grant
OPUS 2014/15/B/ST5/04398 and PRELUDIUM No. 2018/29/N/
ST5/01388). A. Narczyk is grateful to the National Science
Centre of Poland for ETIUDA doctoral scholarship (No. 2018/
28/T/ST5/00267).
28 A. Mitsui, K. Nagao and H. Ohmiya, Org. Lett., 2020, 22,
800–803.
References
1 T. Sehl, Z. Maugeri and D. Rother, J. Mol. Catal. B: Enzym., 29 P.-A. Nocquet, S. Henrion, A. Macé, B. Carboni,
2015, 114, 65–71.
2 M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler,
J. M. Villalgordo and F. Carreaux, Eur. J. Org. Chem., 2017,
1295–1307.
R. Stürmer and T. Zelinski, Angew. Chem., Int. Ed., 2004, 43, 30 E. A. Ilardi, C. E. Stivala and A. Zakarian, Chem. Soc. Rev.,
788–824. 2009, 38, 3133–3148.
3 G. Li, H.-T. Chang and K. B. Sharpless, Angew. Chem., Int. 31 J. Clayden, M. Donnard, J. Lefranc and D. J. Tetlow, Chem.
Ed. Engl., 1996, 35, 451–454.
Commun., 2011, 47, 4624–4639.
4 M. T. Reetz, Chem. Rev., 1999, 99, 1121–1162.
5 S. C. Bergmeier, Tetrahedron, 2000, 56, 2561–2576.
6 F. D. Klingler, Acc. Chem. Res., 2007, 40, 1367–1376.
7 O. N. Burchak and S. Py, Tetrahedron, 2009, 65, 7333–7356.
32 H. Leuser, S. Perrone, F. Liron, F. F. Kneisel and
P. Knochel, Angew. Chem., Int. Ed., 2005, 44, 4627–4631.
33 Z. Li, B. T. Parr and H. M. L. Davies, J. Am. Chem. Soc.,
2012, 134, 10942–10946.
8 T.-X. Métro, B. Duthion, D. G. Pardo and J. Cossy, Chem. 34 M. Arbour, S. Roy, C. Godbout and C. Spino, J. Org. Chem.,
Soc. Rev., 2010, 39, 89–102. 2009, 74, 3806–3814.
9 T. J. Donohoe, C. K. A. Callens, A. Flores, A. R. Lacy and 35 Y. Kobayashi, K. Yamaguchi and M. Morita, Tetrahedron,
A. H. Rathi, Chem. – Eur. J., 2011, 17, 58–76. 2018, 74, 1826–1831.
10 Ch. Weng, H. Zhang, X. Xiong, X. Lu and Y. Zhou, Asian J. 36 A. Narczyk, M. Pieczykolan and S. Stecko, Org. Biomol.
Chem., 2014, 26, 3761–3768. Chem., 2018, 16, 3921–3946.
11 H. Sasai, in Comprehensive Organic Synthesis II, ed. 37 A. Narczyk and S. Stecko, Org. Biomol. Chem., 2020, 18,
P. Knochel and G. A. Molander, Elsevier, Amsterdam, 2014,
ch. 2.13.
12 D. E. Olson, J. Y. Su, D. A. Roberts and J. Du Bois, J. Am.
Chem. Soc., 2014, 136, 13506–13509.
1204–1213.
38 K. M. Cobb, J. M. Rabb-Lynch, M. E. Hoerrner, A. Manders,
Q. Zhou and M. P. Watson, Org. Lett., 2017, 19, 4355–
4358.
13 A. Noble and J. C. Anderson, Chem. Rev., 2013, 113, 2887– 39 F. Chen, Y. Zhang, L. Yu and S. Zhu, Angew. Chem., Int. Ed.,
2939. 2017, 56, 2022–2025.
14 Y.-W. Zhong, Y.-Z. Dong, K. Fang, K. Izumi, M.-H. Xu and 40 K. R. Voigtritter, N. A. Isley, R. Moser, D. H. Aue and
G.-Q. Lin, J. Am. Chem. Soc., 2005, 127, 11956–11957. B. H. Lipshutz, Tetrahedron, 2012, 68, 3410–3416.
15 G.-Q. Lin, M.-H. Xu, Y.-W. Zhong and X.-W. Sun, Acc. Chem. 41 R. Moser, Ž. V. Bošković, C. S. Crowe and B. H. Lipshutz,
Res., 2008, 41, 831–840. J. Am. Chem. Soc., 2010, 132, 7852–7853.
16 G. Masson, S. Py and Y. Vallée, Angew. Chem., Int. Ed., 2002, 42 L. Zygalski, C. Middel, K. Harms and U. Koert, Org. Lett.,
41, 1772–1775. 2018, 20, 5071–5074.
17 O. N. Burchak, C. Philouze, P. Y. Chavant and S. Py, Org. 43 Higher enantioselectivity is observed in case of aryl vinyl
Lett., 2008, 10, 3021–3023.
18 S.-F. Wu, X. Zheng, Y.-P. Ruan and P.-Q. Huang, Org.
Biomol. Chem., 2009, 7, 2967–2975.
19 S.-F. Wu, Y.-P. Ruan, X. Zheng and P.-Q. Huang,
Tetrahedron, 2010, 66, 1653–1660.
ketones than investigated alkyl vinyl ones due better steric
interactions in the transitions state. However, the resulting
benzyl/allyl type alcohols are not suitable materials for our
investigations, since they are unstable and decompose
during a carbamoylation step.
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