Communication
ChemComm
4 P. A. Carvalho, J. W. Comerford, K. J. Lamb, M. North and
P. S. Reiss, Adv. Synth. Catal., 2019, 361, 345–354.
5 M. Sengoden, M. North and A. C. Whitwood, ChemSusChem, 2019,
12, 3296–3303.
6 E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421–431; D. E. Bergbreiter,
C. Hobbs and C. Hongfa, J. Org. Chem., 2011, 76, 523–533; R. Tak,
M. Kumar, T. Menapara, M. K. Choudhary, R. I. Kureshy and
N. H. Khan, ChemCatChem, 2017, 9, 322–328; S. Bai, B. Li, J. Peng,
X. Zhang, Q. Yang and C. Li, Chem. Sci., 2012, 3, 2864–2867.
7 J. A. Castro-Osma, K. J. Lamb and M. North, ACS Catal., 2016, 6, 5012–5025.
8 Structure Elucidation by NMR in Organic Chemistry, ed. E. Breitmaier,
Wiley, Chichester, 1993, pp. 59–60.
approach to the synthesis of this heterocyclic ring system which is
found in many bioactive molecules including: cholesteryl ester
transfer protein inhibitors, prostaglandin D2 receptor antagonists
B, M2 acetylcholine receptor agonists, cholesteryl ester transfer
protein inhibitors and drugs used for HIV infection treatment.20
The authors thank Dr Heather Fish and Dr Alex Hayam for
assistance in recording NMR spectra and Rafael T. Alarcon for
assistance with experimental work.
9 S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa and C. Rizzoli,
Inorg. Chem., 1996, 35, 5995–6003; J. A. Miranda, C. J. Wade and R. D.
Little, J. Org. Chem., 2005, 70, 8017–8026; M. A. Ischay, M. S. Mubarak
and D. G. Peters, J. Org. Chem., 2006, 71, 623–628.
10 J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734–736.
11 An Introduction to Hydrogen Bonding, ed. G. A. Jeffrey, Oxford University
Press, New York, 1997.
12 W. E. Geiger, J. Am. Chem. Soc., 1974, 96, 2632–2634.
13 S. Sachdev, R. Maugi, J. Woolley, C. Kirk, Z. Zhou, S. D. R. Christie
and M. Platt, Langmuir, 2017, 33, 5464–5472.
Conflicts of interest
There are no conflicts of interest to declare.
Notes and references
‡ X-ray data for compounds 3h, f, b, c and a have been deposited with
CCDC with codes 1983169–1983173 respectively.†
14 A. Chaloyard, A. Dormond, J. Tirouflet and N. E. Murr, J. Chem. Soc.,
Chem. Commun., 1980, 214–216; N. Elmurr, A. Chaloyard and
J. Tirouflet, J. Chem. Soc., Chem. Commun., 1980, 446–448.
1 Privileged Chiral Ligands and Catalysts, ed. Q.-L. Zhou, Wiley-VCH,
Weinheim, 2011, ch. 7.
2 K. C. Gupta and A. K. Sutar, Coord. Chem. Rev., 2008, 252, 1420–1450; 15 Y. W. Zhong, Y. Z. Dong, K. Fang, K. Izumi, M. H. Xu and G. Q. Lin,
R. M. Haak, S. J. Wezenberg and A. W. Kleij, Chem. Commun., 2010, 46, J. Am. Chem. Soc., 2005, 127, 11956–11957.
2713–2723; A. Zulauf, M. Mellah, X. Hong and E. Schulz, Dalton Trans., 16 C. Lampard, J. A. Murphy and N. Lewis, J. Chem. Soc., Chem. Commun.,
2010, 39, 6911–6935; S. Matsunaga and M. Shibasaki, Synthesis, 2013, 1993, 295–297.
421–437; S. Matsunaga and M. Shibasaki, Chem. Commun., 2014, 50, 17 N. G. Connelly and W. E. Geiger, Chem. Rev., 1996, 96, 877–910.
1044–1057; R. Irie, T. Uchida and K. Matsumoto, Chem. Lett., 2015, 44, 18 P. Van´ysek, Electrochemical Series in Handbook of Chemistry and
1268–1283; S. Shaw and J. D. White, Chem. Rev., 2019, 119, 9381–9426;
M. Abd El Sater, N. Jaber and E. Schulz, ChemCatChem, 2019, 11,
3662–3687.
3 S. J. Wezenberg and A. W. Kleij, Angew. Chem., Int. Ed., 2008, 47, 2354–2364;
S. Akine and T. Nabeshima, Dalton Trans., 2009, 10395–10408; A. D. Cort,
Physics, ed. W. M. Haynes, CRC Press, London, UK, 93rd edn, 2012,
ch. 5, pp. 80–90.
19 R. C. Pratt and T. D. P. Stack, J. Am. Chem. Soc., 2003, 125, 8716–8717;
F. Thomas, O. Jarjayes, C. Duboc, C. Philouze, E. Saint-Aman and
J. L. Pierre, Dalton Trans., 2004, 2662–2669.
P. De Bernardin, G. Forte and F. Y. Mihan, Chem. Soc. Rev., 2010, 39, 20 M. K. Ghorai, A. K. Sahoo and S. Kumar, Org. Lett., 2011, 13,
3863–3874; M. Andruh, Chem. Commun., 2011, 47, 3025–3042;
S. Akine, J. Inclusion Phenom. Macrocyclic. Chem., 2012, 72, 25–54;
C. J. Whiteoak, G. Salassa and A. W. Kleij, Chem. Soc. Rev., 2012, 41,
622–631; R. M. Clarke and T. Storr, Dalton Trans., 2014, 43,
9380–9391; A. Erxleben, Inorg. Chim. Acta, 2018, 472, 40–57;
G. Yuan, H. Jiang, L. Zhang, Y. Liu and Y. Cui, Coord. Chem. Rev.,
2019, 378, 483–499.
5972–5975; G. D. Xu, G. Q. Yang, Y. Wang, P. L. Shao, J. N. N. Yau,
B. Liu, Y. B. Zhao, Y. Sun, X. X. Xie, S. Wang, Y. Zhang, L. X. Xia and
Y. Zhao, Angew. Chem., Int. Ed., 2019, 58, 14082–14088; R. Y. Huang,
X. K. Chen, C. L. Mou, G. Y. Luo, Y. J. Li, X. Y. Li, W. Xue, Z. C. Jin and
Y. R. Chi, Org. Lett., 2019, 21, 4340–4344; X. Zhang, J. C. Chen,
R. Khan, G. L. Shen, Z. X. He, Y. Y. Zhou and B. M. Fan, Org. Biomol.
Chem., 2019, 17, 10142–10147.
Chem. Commun.
This journal is © The Royal Society of Chemistry 2020