(b) S. W. Coghlan, R. L. Giles, J. A. K. Howard, M. R. Probert, G.
E. Smith and A. Whiting, J. Organomet. Chem., 2005, 690, 4784–4793;
(c) K. Arnold, B. Davies, R. L. Giles, C. Grosjean, G. E. Smith and
A. Whiting, Adv. Synth. Catal., 2006, 348, 813–820; (d) A. J. Blatch, O.
V. Chetina, J. A. K. Howard, L. G. F. Patrick, C. A. Smethurst and
A. Whiting, Org. Biomol. Chem., 2006, 4, 3297–3302;
(e) A. S. Batsanov, D. Hérault, J. A. K. Howard, L. G. F. Patrick, M.
R. Probert and A. Whitig, Organometallics, 2007, 26, 2414–2419;
(f) A. S. Batsanov, C. Grosjean, T. Schütz and A. Whiting, J. Org.
Chem., 2007, 72, 6276–6279; (g) K. Aelvoet, A. S. Batsanov, A.
J. Blatch, L. G. F. Patrick, C. A. Smethurst and A. Whiting, Angew.
Chem., Int. Ed., 2008, 10, 124–134; (h) K. Aelvoet, A. S. Batsanov, A.
J. Blatch, L. G. F. Patrick, C. A. Smethurst and A. Whiting, Angew.
Chem., Int. Ed., 2008, 47, 768–770; (i) K. Arnold, B. Davies, D. Hérault
and A. Whiting, Angew. Chem., Int. Ed., 2008, 350, 2673–2676.
7 K. Arnold, A. S. Batsanov, B. Davies, C. Grosjean, T. Schütz, A. Whiting
and K. Zawatzky, Chem. Commun., 2008, 3879–3881.
and analytical properties were identical to those reported in the
literature.15,16
Acknowledgements
The authors are grateful to One North East and the Department
of Chemistry at Durham University for financial support.
References
1 (a) B. List, A. Lerner and C. F. Barbas, J. Am. Chem. Soc., 2000, 122,
2395–2396; (b) W. Notz and B. List, J. Am. Chem. Soc., 2000, 122,
7386–7387; B. List, Tetrahedron, 2002, 58, 5573–5590.
2 For selected reviews see: (a) L. W. Xu, J. Luo and Y. Lu, Chem.
Commun., 2009, 1807–1821; (b) P. Melchiorre, M. Marigo, A. Carlone
and G. Bartoli, Angew. Chem., Int. Ed., 2008, 47, 6138–6171;
(c) S. Mukherjee, J. W. Yang, S. Hoffmann and B. List, Chem. Rev.,
2007, 107, 5471–5569; (d) A. Erkkila, I. Majander and P. M. Pihko,
Chem. Rev., 2007, 107, 5416–5470; (e) B. List, Chem. Commun., 2006,
819–824.
8 (a) S. S. Chimni and D. Mahajan, Tetrahedron, 2005, 61, 5019–5025;
(b) C. J. Y. Peng, C. Huang, N. Wang, Z. Luo and Y. Jiang, J. Mol. Catal
A: Chem., 2005, 246, 136–139.
9 (a) C. D. Roy and H. C. Brown, J. Organomet. Chem., 2007, 692, 784–
790; (b) C. D. Roy and H. C. Brown, Monatsh. Chem., 2007, 138, 879–
887.
10 (a) D. Hall, Boronic Acids: Preparation and Applications in Organic Syn-
thesis and Medicine, Wiley-VCH, Weinheim, 2005; (b) S. Hermánek,
Chem. Rev., 1992, 92, 325–362; (c) H. Nöth and B. Wreckmeyer, in
Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, ed.
P. Diehl, E. Fluck and R. Kosfeld, NMR Basic Principles and Progress
Series 14, Springer-Verlang, Berlin, 1978.
3 For selected reviews see: (a) E. Marques-Lopez, R. P. Herrera and
M. Christmann, Nat. Prod. Rep., 2010, 27, 1138–1167; (b) S. Bertelsen
and K. A. Jørgensen, Chem. Soc. Rev., 2009, 38, 2178–2189;
(c) A. Dondoni and A. Massi, Angew. Chem., Int. Ed., 2008, 47, 4638–
4660; (d) H. Pellissier, Tetrahedron, 2007, 63, 9267–9331; (e) D. Enders,
C. Grondal and M. R. M. Huettl, Angew. Chem., Int. Ed., 2007, 46,
1570–1581; (f) B. List, Chem. Rev., 2007, 107, 5413–5415;
(g) P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed., 2004, 43, 5138–
5175; (h) A. Berkessel, H. Gröger and D. MacMillan, Asymmetric Orga-
nocatalysis: from Biomimetic Concepts to Applications in Asymmetric
Synthesis, Wiley-VCH, Weinheim, 2005; (i) P. I. Dalko, Enantioselective
Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH,
Weinheim, 2007.
11 G. F. Hennion, P. A. McCusker, E. C. Ashby and A. J. Rutkowski, J. Am.
Chem. Soc., 1957, 79, 5194–5196.
12 K. Burgess and M. Jaspars, Organometallics, 1993, 12, 4197–4200.
13 (a) D. Guillaneux, S. H. Zhao, O. Samuel, D. Rainford and H. B. Kagan,
J. Am. Chem. Soc., 1994, 116, 9430–9439; (b) T. Satyanarayana,
S. Abraham and H. B. Kagan, Angew. Chem., Int. Ed., 2009, 48, 456–
497; (c) S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 2006, 33,
432–440; (d) A. Córdova, W. Zou, P. Dziedzic, I. Ibrahem, E. Reyes and
Y. Xu, Chem.–Eur. J., 2006, 12, 5383–5397; (e) D. G. Blackmond, Acc.
Chem. Res., 2000, 33, 402–411.
14 C. H. Hövelmann and K. Muniz, Chem.–Eur. J., 2005, 11, 3951–3958.
15 Z. Xu, P. Daka and H. Wang, Chem. Commun., 2009, 6825–6827.
16 T. Stern, S. Rückbrod, C. Czekelius, C. Donner and H. Brunner, Adv.
Synth. Catal., 2010, 352, 1983–1992.
17 (a) S. Bahmanyar and K. N. Houk, J. Am. Chem. Soc., 2001, 123, 9922–
9923; (b) S. Bahmanyar and K. N. Houk, J. Am. Chem. Soc., 2001, 123,
11273–11283; (c) S. Bahmanyar, K. N. Houk, H. I. Martin and B. List,
J. Am. Chem. Soc., 2003, 125, 2475–2479; (d) B. List, L. Hoang and
H. J. Martin, Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 5839–5842.
4 I. Georgiou, G. Ilyashenko and A. Whiting, Acc. Chem. Res., 2009, 42,
756–768 and references therein.
5 (a) R. L. Letsinger and S. H. Dandegaonker, J. Am. Chem. Soc., 1959,
81, 498–501; (b) R. L. Letsinger, S. Dandegao, J. D. Morrison and
W. J. Vullo, J. Am. Chem. Soc., 1963, 85, 2223–2227; R. L. Letsinger
and J. D. Morrison, J. Am. Chem. Soc., 1963, 85, 2227–2229;
(c) J. J. Kankare, Synthetic and Molecular Orbital Studies of Some Sub-
stituted Areneboronic Acids Containing Dative Boron–Nitrogen Bonds
and their Catalysis of the Autosolvolysis of 2-Chloroethanol, University
of Torku, 1971.
6 (a) R. L. Giles, J. A. K. Howald, L. G. F. Patrick, M. R. Probert,
G. E. Smith and A. Whiting, J. Organomet. Chem., 2003, 680, 257–262;
2430 | Org. Biomol. Chem., 2012, 10, 2422–2430
This journal is © The Royal Society of Chemistry 2012