Organic & Biomolecular Chemistry
Paper
10 For a selection of reviews on the vinylogous aldol reaction,
see: (a) G. Casiraghi, L. Battistini, C. Curti, G. Rassu and
F. Zanardi, Chem. Rev., 2011, 111, 3076; (b) M. Kalesse, in
Topics in Current Chemistry, ed. J. Mulzer, Springer, Berlin,
2005, pp. 43–76; (c) S. E. Denmark, J. R. Heemstra, Jr. and
G. L. Beutner, Angew. Chem., Int. Ed., 2005, 44, 4682.
Acknowledgements
We thank the EPSRC (EP/F025734/1) and Syngenta for support,
the Isaac Newton–Mays Wild Research Fellowship at Downing
College (M.P.H.), the Herchel Smith Postdoctoral Fellowships
Fund at Cambridge (C.J.C.) and the Deutsche Akademie der
Naturforser Leopoldina (F.A.M.; BMBF-LPD 9901/8-148) for 11 S. Simsek, M. Horzella and M. Kalesse, Org. Lett., 2007, 9,
additional funding, and the EPSRC National Mass Spectro-
metry Centre (Swansea) for mass spectra.
5637.
12 (a) M. T. Crimmins, S. J. Kirincich, A. J. Wells and
A. L. Choy, Synth. Commun., 1998, 28, 3675;
(b) V. V. Samoshin, D. E. Gremyachinskiy, L. L. Smith,
I. V. Bliznets and P. H. Gross, Tetrahedron Lett., 2002, 43,
6329.
13 (a) R. E. Ireland, J. Liu and T. D. Roper, Tetrahedron, 1997,
53, 13221; (b) I. Paterson, M. J. Coster, D. Y.-K. Chen,
J. L. Acena, J. Bach, L. Keown and T. Trieselmann, Org.
Biomol. Chem., 2005, 3, 2420.
Notes and references
1 (a) C. Hertweck, Angew. Chem., Int. Ed., 2009, 48, 4688;
(b) S. M. Dalby and I. Paterson, Curr. Opin. Drug Discovery
Dev., 2010, 13, 777; (c) E. M. Driggers, S. P. Hale, J. Lee and
N. K. Terrett, Nat. Rev. Drug Discovery, 2008, 7, 608; 14 G. Kresze, A. Maschke, R. Albrecht, K. Bederke,
(d) I. Paterson and K.-S. Yeung, Chem. Rev., 2005, 105,
4237; (e) K.-S. Yeung and I. Paterson, Angew. Chem., Int. Ed.,
2002, 41, 4632.
2 (a) H. Shigamori, Y. Tanaka, K. Yazawa, Y. Mikami and
J. Kobayashi, Tetrahedron, 1996, 52, 9031; (b) Y. Tanaka,
H. P. Patzschke, H. Smalla and A. Trede, Angew. Chem., Int.
Ed. Engl., 1962, 1, 80.
15 A. G. Myers, B. H. Yang, H. Chen, L. McKinstry,
D. J. Kopecky and J. L. Gleason, J. Am. Chem. Soc., 1997,
119, 6496.
H. Komaki, K. Yazawa, Y. Mikami, A. Nemoto, T. Tojyo, 16 (a) K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651;
K. Kadawaki, H. Shigemori and J. Kobayashi, J. Antibiot.,
1997, 50, 1036.
(b) A. J. Mancuso, S. L. Huang and D. Swern, J. Org. Chem.,
1978, 43, 2480.
3 (a) Y. Mikami, H. Komaki, T. Imai and K. Yazawa, J. Anti- 17 Y.-S. Hon, L. Lu, R.-C. Chang, S.-W. Lin, P.-P. Sun and
biot., 2000, 53, 70; (b) K. Komatsu, M. Tsuda, Y. Tanaka,
Y. Mikami and J. Kobayashi, J. Org. Chem., 2004, 69, 1535.
4 For a review of the chemistry and biology of immunosup-
C.-F. Lee, Tetrahedron, 2000, 56, 9269.
18 H. C. Kolb, M. S. Van Nieuwenhze and K. B. Sharpless,
Chem. Rev., 1994, 94, 2483.
pressive natural products, see: J. Mann, Nat. Prod. Rep., 19 We thank Dr Robert Paton for carrying out DFT transition
2001, 18, 417.
state calculations on closely related model systems, which
indicated that TS-1 was preferred. (a) R. S. Paton and
J. M. Goodman, J. Org. Chem., 2008, 73, 1253;
(b) R. S. Paton and J. M. Goodman, Org. Lett., 2006, 8, 4299.
5 For a selection of reviews on modern aldol chemistry, see:
(a) S. B. J. Kan, K. K.-H. Ng and I. Paterson, Angew. Chem.,
Int. Ed., 2013, 52, 9097; (b) Modern Methods in Stereo-
selective Aldol Reactions, ed. R. Mahrwald, Wiley-VCH, Wein- 20 See the ESI† for details.
heim, 2013; (c) L. M. Geary and P. G. Hultin, Tetrahedron: 21 For representative applications of the 1,5-anti boron-
Asymmetry, 2009, 20, 131; (d) Modern Aldol Reactions, ed. R.
Mahrwald, Wiley-VCH, Weinheim, 2004.
mediated aldol reaction, see: (a) I. Paterson, D. J. Wallace
and K. R. Gibson, Tetrahedron Lett., 1997, 38, 8911;
(b) I. Paterson and M. Tudge, Tetrahedron, 2003, 59, 6833;
(c) I. Paterson, M. E. Di Francesco and T. Kühn, Org. Lett.,
2003, 5, 599; (d) I. Paterson, M. J. Coster, D. Y.-K. Chen,
K. R. Gibson and D. J. Wallace, Org. Biomol. Chem., 2005, 3,
2410.
6 (a) I. Paterson, F. A. Mühlthau, C. J. Cordier,
M. P. Housden, P. M. Burton and O. Loiseleur, Org. Lett.,
2009, 11, 353; (b) I. Paterson, P. M. Burton, C. J. Cordier,
M. P. Housden, F. A. Mühlthau and O. Loiseleur, Org. Lett.,
2009, 11, 693.
7 (a) I. Paterson, K. R. Gibson and R. M. Oballa, Tetrahedron 22 For a review of asymmetric aldol reactions using boron eno-
Lett., 1996, 37, 8585; (b) D. A. Evans, P. J. Coleman and
B. Côté, J. Org. Chem., 1997, 62, 788; (c) I. Paterson and
lates, see: C. J. Cowden and I. Paterson, Org. React., 1997,
51, 1.
L. A. Collett, Tetrahedron Lett., 2001, 42, 1187; 23 D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am.
(d) D. A. Evans, B. Côté, P. J. Coleman and B. T. Connell, Chem. Soc., 1988, 110, 3560.
J. Am. Chem. Soc., 2003, 125, 10893; (e) L. C. Dias and 24 S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga,
A. M. Aguilar, Chem. Soc. Rev., 2008, 37, 451.
K. B. Hansen, A. E. Gould, M. E. Furrow and
8 (a) A. De Camp Schuda, P. H. Mazzocchi, G. Fritz and
E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 1307.
T. Morgan, Synthesis, 1986, 309; (b) S. A. Burova and 25 D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48,
F. E. McDonald, J. Am. Chem. Soc., 2004, 126, 2495. 4155.
9 A. K. Chatterjee, T.-L. Choi, D. P. Sanders and 26 (a) I. Paterson, J. M. Goodman and M. Isaka, Tetrahedron
R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360.
Lett., 1989, 30, 7121; (b) I. Paterson, G. J. Florence,
This journal is © The Royal Society of Chemistry 2015
Org. Biomol. Chem.